The electrophilic nature of carbenoids, nitrenoids, and oxenoids

Chemical Reviews

Volumn 101, Issue 3, 2001, Pages 697-756

  Boche, Gernot ^a   Lohrenz, John C W ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTROPHILICITY;

ATOMS; CHEMICAL BONDS; ISOTOPES; MOLECULAR STRUCTURE; QUANTUM THEORY; REACTION KINETICS; STEREOCHEMISTRY;

AROMATIC COMPOUNDS;

EID: 0035296971     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr940260x     Document Type: Review

References (527)

1. Footnote 9 in Doering, W.v.E.; Knox, L.H. J. Am. Chem. Soc. 1956, 78, 4947. Historically, it is interesting to mention that the pioneering photolysis of diazomethane in various etheral solvents was performed in Marburg by Meerwein, H.; Rathjen, H.; Werner, H. Ber. Dtsch. Chem. Ges. B 1942, 75, 1610.
2. Footnote 9 in Doering, W.v.E.; Knox, L.H. J. Am. Chem. Soc. 1956, 78, 4947. Historically, it is interesting to mention that the pioneering photolysis of diazomethane in various etheral solvents was performed in Marburg by Meerwein, H.; Rathjen, H.; Werner, H. Ber. Dtsch. Chem. Ges. B 1942, 75, 1610.
3. (a) Closs, G.L.; Closs, L.E. Angew. Chem. 1962, 74, 431.
4. 2 with phenyllithium. G.L. Closs and L.E. Closs were Ph.D. students of Wittig in Heidelberg. Another pioneer in carbenoid chemistry, G. Köbrich, did his Habilitationsarbeit at Wittig's institute.
5. Etter, R.M.; Skovronek, H.S.; Skell, P.S. J. Am. Chem. Soc. 1959, 81, 1008.
6. Closs, G.L.; Mass, R.A. J. Am. Chem. Soc. 1964, 86, 4042.
7. The term "carbenoid" as an adjective (and not as a noun as in ref 4) was actually used first by Friedman, L.; Shechter, H. J. Am. Chem. Soc. 1959, 81, 5512, to describe the base-catalyzed decomposition of tosylhydrazones in aprotic solvents, implying the probable intermediacy of carbenes. Volpin, M.E.; Koreshov, Y.D.; Dulanova, V.G.; Kursanov, D.N. Tetrahedron 1962, 18, 107, named carbene-analogues, in which carbon is replaced by another element, "carbenoids".
8. The term "carbenoid" as an adjective (and not as a noun as in ref 4) was actually used first by Friedman, L.; Shechter, H. J. Am. Chem. Soc. 1959, 81, 5512, to describe the base-catalyzed decomposition of tosylhydrazones in aprotic solvents, implying the probable intermediacy of carbenes. Volpin, M.E.; Koreshov, Y.D.; Dulanova, V.G.; Kursanov, D.N. Tetrahedron 1962, 18, 107, named carbene-analogues, in which carbon is replaced by another element, "carbenoids".
9. Review articles on carbenoids (and in some cases on carbenes): (a) Hine, J. Divalent Carbon; Ronald Press: New York, 1964.
10. (b) Kirmse, W. Angew. Chem. 1965, 77, 1; Angew. Chem. Int. Ed. Engl. 1965, 4, 1.
11. (b) Kirmse, W. Angew. Chem. 1965, 77, 1; Angew. Chem. Int. Ed. Engl. 1965, 4, 1.
12. (c) Köbrich, G. Angew. Chem. 1965, 77, 75; Angew. Chem., Int. Ed. Engl. 1965, 4, 49.
13. (c) Köbrich, G. Angew. Chem. 1965, 77, 75; Angew. Chem., Int. Ed. Engl. 1965, 4, 49.
14. (d) Köbrich, G. Angew. Chem. 1972, 84, 557; Angew. Chem., Int. Ed. Engl. 1972, 11, 473.
15. (d) Köbrich, G. Angew. Chem. 1972, 84, 557; Angew. Chem., Int. Ed. Engl. 1972, 11, 473.
16. (e) Kirmse, W. Carbene, Carbenoide, Carbenanaloga; Verlag Chemie: Weinheim, 1969.
17. (f) Kirmse, W. Carbene Chemistry, 2nd ed.; Academic Press: New York, 1971.
18. (g) Moss, R.A. In Carbenes; Jones, M., Jr., Moss, R.A., Eds.; Wiley-Interscience: New York, 1973; Vol. I, pp 260, 285.
19. (h) Seyferth, D. In Carbenes; Jones, M., Jr., Moss, R.A., Eds.; Wiley-Interscience: New York, 1975; Vol. 2, p 101.
20. (i) Jones, M., Jr.; Moss, R.A. Carbenes. In Reactive Intermediates; Jones, M., Jr., Moss, R.A., Eds.; Wiley-Interescience: New York, 1978; Vol. 1, p 82.
21. (j) Jones, M., Jr.; Moss, R.A. Carbenes. In Reactive Intermediates; Jones, M., Jr., Moss, R.A., Eds.; Wiley-Interscience: New York, 1981; Vol. 2, p 79.
22. (k) Jones, M., Jr.; Moss, R.A. Carbenes. In Reactive Intermediates; Jones, M., Jr., Mess, R.A., Eds.; Wiley-Interscience: New York, 1985; Vol. 3, p 62.
23. (l) Siegel, H. Top. Curr. Chem. 1982, 106, 55.
24. (m) Taylor, K.G. Tetrahedron 1982, 38, 2751.
25. (n) Stang, P.J. Chem. Rev. 1978, 78, 383. In the following review articles carbenoids (and carbenes) are not treated exclusively.
26. (o) Schöllkopf, U. In Houben-Weyl-Müller, Methoden der organischen Chemie; Georg Thieme Verlag: Stuttgart, 1970; Vol. 13/1, p 87.
27. (p) Chivers, T. Organomet. Chem. Rev. 1970, A6, 1.
28. (q) Wakefield, B.J.Li- and MgX-Compounds. In Comprehensive Organometallic Chemistry; Wilkinson, G., Ed.; Pergamon Press: Oxford, 1982; Vol 7, p 1.
29. (r) Boersma, J. Zn-compounds. In Comprehensive Organometallic Chemistry; Wilkinson, G., Ed.; Pergamon Press: Oxford, 1982; Vol. 2, p 823.
30. (s) Boche, G.; Walborsky, H.M. Cyclopropane Derived Reactive Intermediates, Updates from the Chemistry of Functional Groups; Patai, S., Rappoport, Z., Eds.; J. Wiley: New York, 1990; Chapter 4.
31. (t) Gray, M.; Tinkl, M.; Snieckus, V. Li-compounds. In Comprehensive Organometallic Chemistry II; Abel; E.W., Stone, F.G.A., Wilkinson, G., Eds.; Pergamon Press: New York, 1995, Vol. 11, p 1.
32. (u) Brown, J.M.; Armstrong, S.K. MgX-compounds. In Comprehensive Organometallic Chemistry II; Abel, E.W., Stone, F.G.A., Wilkinson, G., Eds.; Pergamon Press: New York, 1995, Vol. 11, p 129.
33. (v) Knochel, P. Zn-compounds. In Comprehensive Organometallic Chemistry II; Abel, E.W., Stone, F.G.A., Wilkinson, G., Eds.; Pergamon Press: New York, 1995; Vol. 11, p 159.
34. (w) Braun, M. Angew. Chem. 1998, 110, 444; Angew. Chem., Int. Ed. Engl. 1998, 37, 7, 430.
35. (w) Braun, M. Angew. Chem. 1998, 110, 444; Angew. Chem., Int. Ed. Engl. 1998, 37, 7, 430.
36. (x) A comprehensive treatment on carbenes (carbenoids) has also been published in Houben-Weyl, Methoden der organischen Chemie; Regitz, M., Ed.; Georg Thieme Verlag: Stuttgart, 1989; E19b, Vols. 1 and 2.
37. (y) Bettinger, H.F.; Schleyer, P.v.R.; Schreiner, P.R.; Schaefer, H.F., III. In The Encyclopedia of Computational Chemistry; Schleyer, P.v.R., Allinger, N.L., Clark, T., Gasteiger, J., Kollman, P.A., Schaefer, H.F., III, Schreiner, P.R., Eds.; John Wiley & Sons: Chichester, 1998; pp 183-196.
38. Seyferth, D.; Welch, D.E.; Raab, G. J. Am. Chem. Soc. 1962, 84, 4266.
39. Köbrich, G.; Trapp, H.Z. Naturforsch. 1963, 18b, 1125.
40. (a) Fritsch, P. Liebigs Ann. Chem. 1894, 279, 319.
41. (b) Buttenberg, W.P. Liebigs Ann. Chem. 1894, 279, 324.
42. (c) Wiechell, H. Liebigs Ann. Chem. 1894, 279, 337.
43. Bothner-By, A.A. J. Am. Chem. Soc. 1955, 77, 3293.
44. (a) Curtin, D.Y.; Flynn, E.W. J. Am. Chem. Soc. 1959, 81, 4714.
45. (b) Curtin, D.Y.; Flynn, E.W.; Nystrom, R.F. J. Am. Chem. Soc. 1958, 80, 4599.
46. Simanetta, M.; Carra, S. Tetrahedron 1963, 19, Suppl 2, 467.
47. Goldstein, M.J.; Dolbier, W.R., Jr. J. Am. Chem. Soc. 1965, 87, 2293.
48. (a) Kirmse, W.; Wächtershäuser, G. Tetrahedron 1966, 22, 73.
49. (b) Other C-H insertion reactions: Corey, R.M.; Burton, L.P. J.; Pecherle, R.G. Synth. Commun. 1979, 9, 735.
50. (a) Seyferth, D., Lambert, R.L., Jr.; Hanson, E.M. J. Organomet. Chem. 1970, 24, 647.
51. (b) Villieras, J. Organomet. Chem. Rev., Sect. A. 1971, 7, 81.
52. (c) Hahn, R.C.; Tompkins, J. Tetrahedron Lett. 1990, 31, 937.
53. (d) Hoffmann, R.W.; Kusehe, A. Chem. Ber. 1994, 127, 1311.
54. (a) Simmons, H.E.; Smith, R.D. J. Am. Chem. Soc. 1958, 80, 5323.
55. (b) Simmons, H.E.; Smith, R.D. J. Am. Chem. Soc. 1959, 81, 4256.
56. (c) Wittig, G.; Schwarzenbach, K. Liebigs Ann. Chem. 1962, 650, 1.
57. (d) Simmons, H.E.; Cairns, T.L.; Vladuchick, S.A.; Hoiness, C.M. Org. React. 1973, 20, 1 and earlier references cited.
58. (e) Review of the Simmons-Smith reagent: Charette, A.B.; Marcoux, J.-F. Synlett 1995, 1197.
59. (f) Furukawa, J.; Kawabata, N.; Nishimura, J. Tetrahedron Lett. 1966, 3353.
60. (g) Charette, A.B.; Marcoux, J.-F. J. Am. Chem. Soc. 1996, 118, 4539.
61. (a) Hoberg, H. Liebigs Ann. Chem. 1962, 656, 1.
62. (b) Kauffmann, T.; Fobker, R.; Wensing, M. Angew. Chem. 1988, 100, 1005; Angew. Chem., Int. Ed. Engl. 1988, 27, 943.
63. (b) Kauffmann, T.; Fobker, R.; Wensing, M. Angew. Chem. 1988, 100, 1005; Angew. Chem., Int. Ed. Engl. 1988, 27, 943.
64. (c) Ukaji, Y.; Inomata, K. Chem. Lett., 1992, 2353.
65. (a) It is interesting to mention that Wittig concluded from his studies of halogen-metal exchange reactions with aliphatic halides in 1941 that species with lithium and halogen at the same carbon atom (later called Li/Hal carbenoids) have "a high mobilitiy" ("grosse Beweglichkeit") of the halogen atom, see ref 2b.
66. (b) Wittig, G.; Harborth, G. Ber. Dtsch. Chem. Ges. 1944, 77-79, 306 and 315. Wittig also pointed out that the metal should assist in this "high mobility"; see also ref 19.
67. 18.
68. Closs, G.L.; Coyle, J.J. J. Am. Chem. Soc. 1962, 84, 4350.
69. Closs, G.L.; Coyle, J.J. J. Am. Chem. Soc. 1965, 87, 4270.
70. Köbrich, G.; Flory, K.; Merkle, H.R. Tetrahedron Lett. 1965, 973.
71. Köbrich, G.; Flory, K.; Fischer, R.H. Chem. Ber. 1966, 99, 1793.
72. Hoeg, D.F.; Lusk, D.I.; Crumbliss, A.L. J. Am. Chem. Soc. 1965, 87, 4147.
73. Miller, W.T., Jr.; Whalen, D.M. J. Am. Chem. Soc. 1964, 86, 2089.
74. Moss, R.A.; Pilkiewicz, F.G. J. Am. Chem. Soc. 1974, 96, 5632.
75. (a) Skattebøl, L. Chem. Ind. 1962, 2146.
76. (b) L. Skattebøl, Tetrahedron 1967, 23, 1107.
77. (c) Reviews: Jones, W.M. In Rearrangments in Ground and Excited States; DeMayo, P., Ed.; Academic Press: New York; 1980.
78. (d) Weyerstrahl, P. In The Chemistry of Functional Groups, Suppl. D; Patai, S., Rappoport, Z.J. Wiley: New York; p 1451.
79. (e) Boche, G.; Walborsky, H.M. Cyclopropane Derived Reactive Intermediates, Updates from the Chemistry of Functional Groups; Patai. S., Rappoport, Z., Eds.; J. Wiley: New York, 1990; p 195.
80. Warner, P.M.; Herold, R.D. J. Org. Chem. 1983, 48, 5411.
81. The stereochemical aspects of the Skattebøl rearrangement have been nicely reviewed by Moss and Jones in ref 6j, p 113.
82. Huisgen, R.; Burger, U. Tetrahedron Lett. 1970, 3053.
83. Stiasny, H.C.; Hoffmann, R.W. Chem. Eur. J. 1995, 1, 619.
84. Mareda, J.; Rondan, N.G.; Houk, K.N.; Clark, T.; Schleyer, P.V.R. J. Am. Chem. Soc. 1983, 105, 6997.
85. Hoveyda, A.H.; Evans, D.A.; Fu, G.C. Chem. Rev. 1993, 93, 1307.
86. Bernardi, F.; Bottoni, A.; Miscione, G.P. J. Am. Chem. Soc. 1997, 119, 12300.
87. (a) Villieras, J.; Bacquet, C.; Normant, J.F. J. Organomet. Chem. 1972, 40, C1.
88. (b) Villieras, J.; Bacquet, C.; Normant, J.F. C. R. Acad. Sci. Ser. C 1973, 276, 433.
89. (c) Villieras, J.; Bacquet, C.; Normant, J.F. J. Organomet. Chem. 1975, 97, 325.
90. (d) Villieras, J.; Bacquet, C.; Normant, J.F. J. Organomet. Chem. 1975, 97, 355.
91. Köbrich, G.; Grosset, J. Tetrahedron Lett. 1972, 4117.
92. (a) Taguchi, H.; Yamamoto, H.; Nozaki, H. Tetrahedron Lett. 1972, 4661.
93. (b) Taguchi, H.; Yamamoto, H.; Nozaki, H. J. Am. Chem. Soc. 1974, 96, 3010.
94. Taguchi, H.; Yamamoto, H.; Nozaki, H. J. Am. Chem. Soc. 1974, 96, 6510.
95. Taguchi, H.; Yamamoto, H.; Nozaki, H. Bull. Chem. Soc. Jpn. 1977, 50, 1592. See also Nozaki, H. Synlett 1990, 441.
96. Taguchi, H.; Yamamoto, H.; Nozaki, H. Bull. Chem. Soc. Jpn. 1977, 50, 1592. See also Nozaki, H. Synlett 1990, 441.
97. Vedejs, E.; Shepherd, R.A. J. Org. Chem. 1976, 41, 742.
98. Ward, H.D.; Teager, D.S.; Murray, R.K., Jr. J. Org. Chem. 1992, 57, 1926.
99. Not unexpectedly, carbenoid reactions similar to those shown in Scheme 11 were also observed with β-oxido-lithio-dithioacetals as reported by Abraham, W.D.; Bhupathy, M.; Cohen, T. Tetrahedron Lett. 1987, 28, 2203. Such ring-expansion reactions of Li/Hal and Li/SR carbenoids are of great significance in organic synthesis; see also the review articles in refs 61, 6m, 6w, and ref 43.
100. (a) Satoh, T.; Itoh, N.; Gengyo, K.; Takada, S.; Asakawa, N.; Yamani, Y.; Yamakawa, K. Tetrahedron 1994, 50, 11839. These authors also provide a review on the pertinent literature.
101. (b) An analogous method was recently used for the preparation of α-chloroalkylmagnesium compounds with >90% ee, Hoffmann R.W.; Nell, P.G. Angew. Chem. 1999, 111, 354; Angew. Chem., Int. Ed. 1999, 38, 338.
102. (b) An analogous method was recently used for the preparation of α-chloroalkylmagnesium compounds with >90% ee, Hoffmann R.W.; Nell, P.G. Angew. Chem. 1999, 111, 354; Angew. Chem., Int. Ed. 1999, 38, 338.
103. Taylor, K.G.; Chaney, J.; Deck, J.C. J. Am. Chem. Soc. 1976, 98, 4163.
104. Oku, A.; Harada, T.; Hattori, K.; Nozaki, Y.; Yamaura, Y. J. Org. Chem. 1988, 53, 3089. The reader is also referred to the work of Ritter, R.H.; Cohen, T. J. Am. Chem. Soc. 1986, 108, 3718, who concluded in related studies that a hydride is transferred from α-oxyanions onto carbenoids.
105. Oku, A.; Harada, T.; Hattori, K.; Nozaki, Y.; Yamaura, Y. J. Org. Chem. 1988, 53, 3089. The reader is also referred to the work of Ritter, R.H.; Cohen, T. J. Am. Chem. Soc. 1986, 108, 3718, who concluded in related studies that a hydride is transferred from α-oxyanions onto carbenoids.
106. (a) Lüttringhaus, A.; v. Sääf, G. Angew. Chem. 1938, 51, 915.
107. (b) See also Lüttringhaus, A.; Wagner-v. Sääf, G.; Sucker, E.; Borth, G. Liebigs Ann. Chem. 1947, 557, 46.
108. Wittig, G.; Löhmann, L. Liebigs Ann. Chem. 1942, 550, 260.
109. Review on reactions of ethers with organolithium reagents: Maercker, A. Angew. Chem. 1987, 99, 1002; Angew. Chem., Int. Ed. Engl. 1987, 26, 972 and earlier references cited.
110. Review on reactions of ethers with organolithium reagents: Maercker, A. Angew. Chem. 1987, 99, 1002; Angew. Chem., Int. Ed. Engl. 1987, 26, 972 and earlier references cited.
111. Kirmse, W.; Wedel, v.B. Liebigs Ann. Chem. 1963, 666, 1.
112. Köbrich, G.; Ansari, F. Chem. Ber. 1967, 100, 2011.
113. Kitatani, K.; Yamamoto, H.; Hiyama, T.; Nozaki, H. Bull. Chem. Soc. Jpn. 1977, 50, 2158.
114. (a) Duraisamy, M.; Walborsky, H.M. J. Am. Chem. Soc. 1984, 106, 5085.
115. (b) Walborsky, H.M.; Duraisamy, M. Tetrahedron Lett. 1985, 26, 2743.
116. (c) Rachon, J.; Goedken, V.; Walborsky; H.M. J. Am. Chem. Soc. 1986, 108, 7435.
117. (d) Topolski, M.; Duraisamy, M.; Rachon, J.; Gawronski, J.; Gawronska, K.; Goedken, V.; Walborsky, H.M. J. Org. Chem. 1993, 58, 546.
118. (a) Harada, T.; Hattori, K.; Katsuhira, T.; Oku, A. Tetrahedron Lett. 1989, 30, 6035.
119. (b) Harada, T.; Kotani, Y.; Katsuhira, T.; Oku, A. Tetrahedron Lett. 1991, 32, 1573.
120. (c) Harada, T.; Katsuhira, T.; Hattori, K.; Oku, A. J. Org. Chem. 1993, 58, 2958.
121. (d) Harada, T.; Katsuhira, T.; Hara, D.; Kotani, Y.; Maejima, K.; Kaji, R.; Oku, A. J. Org. Chem. 1993, 58, 4897.
122. (a) Kocienski, P.; Wadman, S.; Cooper, K. J. Am. Chem. Soc. 1989, 111, 2363.
123. (b) Kocienski, P.; Barber, C. Pure Appl. Chem. 1990, 62, 1933.
124. Boche, G.; Bosold, F.; Lohrenz, J.C.W.; Opel, A.; Zulauf, P. Chem. Ber. 1993, 126, 1873.
125. (a) Another example of a stereoselective substitution at a vinylic carbenoid carbon atom may be hidden in the work of Duhamel, L.; Poirier, J.M. J. Org. Chem. 1979, 44, 3585. More recent reactions of carbenoids (or carbenes) with nucleophiles are found in the following references.
126. (b) Eisch, J.J.; McNulty, J.F.; Shi, X. J. Org. Chem. 1994, 59, 7.
127. (c) Fleming, I.; Ghosh, U.; Mack, S.R.; Clark, B.P. Chem. Commun. 1998, 711.
128. (d) Fleming, I.; Mack, S.R.; Clark, B.P. Chem. Commun. 1998, 713.
129. (e) Fleming, I.; Mack, S.R.; Clark, B.P. Chem. Commun. 1998, 715.
130. (a) Köbrich, G.; Merkle, H.R. Chem. Ber. 1966, 99, 1782.
131. (b) See also Arct, J.; Skattebøl, L. Acta Chem. Scand. 1982, B36, 593.
132. Morken, P.A.; Bachand, P.C.; Swenson, D.C.; Burton, D.J. J. Am. Chem. Soc. 1993, 115, 5430.
133. See also Doering, W.v.E.; Hoffmann, A.K. J. Am. Chem. Soc. 1954, 76, 6162.
134. Köbrich, G.; Fischer, R.H. Tetrahedron 1968, 24, 4343.
135. Miller, W.T.; Kim, C.S.Y. J. Am. Chem. Soc. 1959, 81, 5008.
136. Köbrich, G.; Büttner, H.; Wagner, E. Angew. Chem. 1970, 82, 177; Angew. Chem., Int. Ed. Engl. 1970, 9, 169.
137. Köbrich, G.; Büttner, H.; Wagner, E. Angew. Chem. 1970, 82, 177; Angew. Chem., Int. Ed. Engl. 1970, 9, 169.
138. Schlosser, M.; Spahic, B.; Le Van Chau Helv. Chim. Acta 1975, 58, 2586.
139. Seebach, D.; Beck, A.K. J. Am. Chem. Soc. 1969, 91, 1540.
140. Paulino, J.A.; Squires, R.R. J. Am. Chem. Soc. 1991, 113, 5573.
141. (a) Scheibler, H.; Beiser, W.; Krabbe, W. J. Prakt. Chem. 1932, 133, 131.
142. (b) Scheibler, H.; Schmidt, A. Chem. Ber. 1933, 66, 501.
143. (c) Scheibler, H.; Beiser, W.; Cobler, H.; Schmidt, A. Chem. Ber. 1934, 67, 1507.
144. (d) Scheibler, H.; Schmidt, A. Chem. Ber. 1934, 67, 1514.
145. (e) Scheibler, H.; Schmidt, H.-J. Ber. Dtsch. Chem. Ges. B 1936, 69, 12.
146. (a) Review: Wanzlick, H.-W. Angew. Chem. 1962, 74, 129; Angew. Chem., Int. Ed. Engl. 1962, 1, 75.
147. (a) Review: Wanzlick, H.-W. Angew. Chem. 1962, 74, 129; Angew. Chem., Int. Ed. Engl. 1962, 1, 75.
148. (b) Schönherr, H.-J.; Wanzlick, H.W. Chem. Ber. 1970, 103, 1037, cit. lit.
149. (a) Arduengo, A.J., III; Harlow, R.L.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361.
150. (b) Arduengo, A.J., III; Goerlich, J.R.; Marshall, W.J. J. Am. Soc. Chem. 1995, 117, 11027 and references cited.
151. (c) Arduengo, A.J., III; Goerlich, J.R.; Marshall, W.J. Liebigs Ann./Recueil 1997, 365. Reviews.
152. Regitz, M. Angew. Chem. 1996, 108, 791; Angew. Chem., Int. Ed. Engl. 1996 35, 725.
153. (d) Regitz, M. Angew. Chem. 1996, 108, 791; Angew. Chem., Int. Ed. Engl. 1996 35, 725.
154. (e) Arduengo, A.J., III; Kafczyk, R. Chem. Unserer Zeit 1998, 32, 6. Theoretical investigations and further literature.
155. (f) Heinemann, C.; Müller, T.; Apeloig, Y.; Schwarz, H. J. Am. Chem. Soc. 1996, 118, 2023.
156. (g) Boehme, C.; Frenking, G. J. Am. Soc. Chem. 1996, 118, 2039.
157. (h) Boche, G.; Andrews, P.; Harms, K.; Marsch, M.; Rangappa, K.S.; Schimeczek, M.; Willeke, C. J. Am. Chem. Soc. 1996, 118, 4925, Recent work.
158. (i) Alder, R.W.; Butts, C.P.; Orpen, A.G. J. Am. Chem. Soc. 1998, 120, 11526 and earlier literature cited.
159. Moss, R.A.; Fan, H.; Gurumurthy, R.; Ho, G.-J. J. Am. Chem. Soc. 1991, 113, 1435.
160. Clark, T.; Schleyer, P.v.R. J. Chem. Soc., Chem. Commun. 1979, 883.
161. Rohde, C.; Clark, T.; Kaufmann, E.; Schleyer, P.v.R. J. Chem. Soc., Chem. Commun. 1982, 882.
162. Luke, B.T.; Pople, J.A.; Schleyer, P.v.R.; Clark, T. Chem. Phys. Lett. 1983, 102, 148.
163. Schleyer, P.v.R.; Clark, T.; Kos, A.J.; Spitznagel, G.W.; Rohde, C.; Arad, D.; Houk, K.N.; Rondan, N.G. J. Am. Chem. Soc. 1984, 106, 6467.
164. Hehre, W.J.; Radom, L.; Schleyer, P.v.R.; Pople, J.A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
165. Vincent, M.A., Schaefer, H.F., III. J. Chem. Phys. 1982, 77, 6103.
166. Abronin, I.A.; Zagradnik, R.; Zhidomirov, G.M. J. Struct. Chem. 1980, 21, 3.
167. Clark, T.; Schleyer, P.v.R. Tetrahedron Lett. 1979, 51, 4963.
168. Clark, T.; Schleyer, P.v.R. J. Am. Chem. Soc. 1979, 101, 7747.
169. (a) Andrews, L.; Carver, T.G. J. Phys. Chem. 1968, 72, 1743.
170. (b) Hatzenbühler, D.A.; Andrews, L.; Carey, F.A. J. Am. Chem. Soc. 1975, 97, 187.
171. Clark, T.; Schleyer, P.v.R.; Houk, K.N.; Rondan, N.G. J. Chem. Soc., Chem. Commun. 1981, 579.
172. Boche, G.; Opel, A.; Marsch, M.; Harms, K.; Haller, F.; Lohrenz, J.C.W.; Thümmler, C.; Koch, W. Chem. Ber. 1992, 125, 2265.
173. Boche, G.; Lohrenz, J.C.W.; Opel, A. In Lithium Compounds: Principles and Applications; Schleyer, P.v.R., Sapse, A.-M., Eds.; J. Wiley & Sons: New York, 1993; p 195.
174. Bernardi, F.; Csizmadia, I.G.; Mangini, A.; Schlegel, H.B.; Whangbo, M.-H.; Wolfe, S. J. Am. Chem. Soc. 1975, 97, 2209 and earlier literature of S. Wolfe cited there.
175. Bernardi, F.; Bottoni, A.; Venturini, A.; Mangini, A. J. Am. Chem. Soc. 1986, 108, 8171.
176. Boche, G.; Lohrenz, J.C.W.; Cioslowski, J.; Koch, W. In The Chemistry of Sulphur Containing Functional Groups. Supplement S; Patai, S., Rappoport, Z., Eds.; J. Wiley & Sons: Chichester, 1993; p 339.
177. Amstutz, R.; Laube, T.; Schweizer, W.B.; Seebach, D.; Dunitz, J.D. Helv. Chim. Acta 1984, 67, 224.
178. Seebach, D.; Maetzke, T.; Haynes, R.K.; Paddon-Row: M.N.; Wang, S.S. Helv. Chim. Acta 1988, 71, 299.
179. Zarges, W.; Marsch, M.; Harms, K.; Koch, W.; Frenking, G.; Boche, G. Chem. Ber. 1991, 124, 543.
180. Boche, G. Angew. Chem. 1989, 101, 286; Angew. Chem., Int. Ed. Engl. 1989, 28, 277.
181. Boche, G. Angew. Chem. 1989, 101, 286; Angew. Chem., Int. Ed. Engl. 1989, 28, 277.
182. Wang, B.; Dang, C. Chem. Phys. Lett. 1988, 147, 99.
183. Wang, B.; Dang, C.; Xu, L.; Tao, F. Chem. Phys. Lett. 1989, 161, 388.
184. Lohrenz, J.C.W.; Boche, G. Unpublished work.
185. Bergner, A.; Dolg, M.; Küchle, W.; Stoll, H.; Preuss, H. Mol. Phys. 1993, 80, 1431.
186. (a) Seebach, D.; Siegel, H.; Müllen, K.; Hiltbrunner, K. Angew. Chem. 1979, 91, 844; Angew. Chem., Int. Ed. Engl. 1979, 18, 784.
187. (a) Seebach, D.; Siegel, H.; Müllen, K.; Hiltbrunner, K. Angew. Chem. 1979, 91, 844; Angew. Chem., Int. Ed. Engl. 1979, 18, 784.
188. (b) Siegel, H.; Hiltbrunner, K.; Seebach, D. Angew. Chem. 1979, 91, 845; Angew. Chem., Int. Ed. Engl. 1979, 18, 785.
189. (b) Siegel, H.; Hiltbrunner, K.; Seebach, D. Angew. Chem. 1979, 91, 845; Angew. Chem., Int. Ed. Engl. 1979, 18, 785.
190. (c) Seebach, D.; Siegel, H.; Gabriel, J.; Hässig, R. Helv. Chim. Acta 1980, 63, 2046.
191. (d) Seebach, D.; Hässig, R.; Gabriel, J. Helv. Chim. Acta 1983, 66, 308.
192. (e) Seebach, D.; Gabriel, J.; Hässig, R. Helv. Chim. Acta 1984, 67, 1083.
193. Harder, S.; Boersma, J.; Brandsma, L.; Kanters, J.A.; Bauer, W.; Pi, R.; Schleyer, P.v.R.; Schöllhorn, H.; Thewalt, U. Organometallics 1989, 8, 1688.
194. Hailer, F. Ph.D. work, Universität Marburg, 1994.
195. Sorger, K.; Bauer, W.; Schleyer, P.v.R.; Stalke, D. Angew. Chem. 1995, 107, 1766; Angew. Chem., Int. Ed. Engl. 1995, 34, 1594.
196. Sorger, K.; Bauer, W.; Schleyer, P.v.R.; Stalke, D. Angew. Chem. 1995, 107, 1766; Angew. Chem., Int. Ed. Engl. 1995, 34, 1594.
197. (a) Canepa, C.; Antoniotti, P.; Tonachini, G. Tetrahedron 1994, 50, 8073.
198. (b) Canepa, C.; Tonachini, G. Tetrahedron 1994, 50, 12511.
199. Doering, W.v.E.; La Flamme, P.M. Tetrahedron 1958, 2, 75.
200. (a) Köbrich, G. Angew. Chem. 1967, 79, 15; Angew. Chem., Int. Ed. Engl. 1967, 6, 41.
201. (a) Köbrich, G. Angew. Chem. 1967, 79, 15; Angew. Chem., Int. Ed. Engl. 1967, 6, 41.
202. (b) Köbrich, G.; Flory, K.; Drischel, W. Angew. Chem. 1964, 76, 536; Angew. Chem., Int. Ed. Engl. 1964, 3, 513.
203. (b) Köbrich, G.; Flory, K.; Drischel, W. Angew. Chem. 1964, 76, 536; Angew. Chem., Int. Ed. Engl. 1964, 3, 513.
204. Moser, W.R. J. Am. Chem. Soc. 1969, 91, 1135.
205. Rondan, N.G.; Hank, K.N.; Moss, R.A. J. Am. Chem. Soc. 1980, 102, 1770.
206. Hirai, A.; Nakamura, M.; Nakamura, E. Chem. Lett. 1998, 927.
207. Moreno, M.; Lluch, J.M.; Oliva, A.; Bertrán, J. J. Phys. Chem. 1988, 92, 4180.
208. Zurawski, B.; Kutzelnigg, W. J. Am. Chem. Soc. 1978, 100, 2654.
209. Baild, M.S. Annu. Rep. Prog. Chem., Sect. B 1984, 81, 79.
210. Tomioka, H.; Tabayashi, K.; Ozaki, Y.; Izawa, Y. Tetrahedron 1985, 41, 1435.
211. Boche, G.; Bosold, F.; Hermann, H.; Marsch, M.; Harms, K.; Lohrenz, J.C.W. Chem. Eur. J. 1998, 4, 814.
212. Hermann, H.; Lohrenz, J.C.W.; Kühn, A.; Boche, G. Tetrahedron 2000, 56, 4109.
213. Schöllkopf, U.; Eisert, M. Liebigs Ann. Chem. 1963, 664, 76.
214. Dargel, T.K.; Koch, W. J. Chem. Soc., Perkin Trans. 2, 1996, 877.
215. Nakamura, E.; Hirai, A.; Nakamura, M. J. Am. Chem. Soc. 1998, 120, 5844, and ref. cited.
216. 2Cl 144 isomers were calculated by Qui, H.; Deng, C. Chem. Phys. Lett. 1996, 249, 279.
217. Nayera, C.; Yus, M.; Hässig, R.; Seebach, D. Helv. Chim. Acta 1984, 67, 1100.
218. (a) Cope, A.C.; Berchtold, G.A.; Peterson, P.E.; Sharman, S.H. J. Am. Chem. Soc. 1960, 82, 6370.
219. (b) Cope, A.C.; Brown, M.; Lee, H.-H. J. Am. Chem. Soc. 1958, 80, 2855.
220. (e) Cope, A.C.; Lee, H.-H.; Petree, H.E. J. Am. Chem. Soc. 1958, 80, 2849.
221. (a) Crandall, J.K.; Lin, L.-H.C. J. Am. Chem. Soc. 1967, 89, 4526.
222. (b) Review: Crandall, J.K.; Apparu, M. Org. React. 1983, 29, 345.
223. Further reactions of α-lithiated oxiranes: (a) Eisch, J.J.; Galle, J.E. J. Am. Chem. Soc. 1976, 98, 4646.
224. (b) Eisch, J.J.; Galle, J.E. J. Organomet. Chem. 1988, 341, 293.
225. (c) Eisch, J.J.; Galle, J.E. J. Org. Chem. 1990, 55, 4835.
226. (d) Molander, G.A.; Mautner, K. J. Org. Chem. 1989, 54, 4042.
227. (e) Lohse; P.; Loner, H.; Acklin, P.: Sternfeld. F.; Pfaltz, A. Tetrahedron Lett. 1991, 32, 615.
228. (f) Taniguchi, M.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1991, 32, 2783.
229. (g) Soderquist, J.A.; Lopez, C. Tetrahedron Lett. 1991, 32, 6305.
230. (a) Kutzelnigg, W.; Fleischer, U.; Schindler, M. In NMR, Basic Principles and Progress; Springer: New York, 1990; Vol. 23, pp 165-262.
231. (b) Kutzelnigg, W. Isr. J. Chem. 1986, 19, 193.
232. (c) Kutzelnigg, W. J. Mol. Struct. (THEOCHEM) 1989, 202, 11.
233. (d) Schindler, M.; Kutzelnigg, W. J. Chem. Phys. 1982, 76, 1919.
234. Bühl, M.; von Eikema Hommes, N.J.R.; Schleyer, P.v.R.; Fleischer, U.; Kutzelnigg, W. J. Am. Chem. Soc. 1991, 113, 2459.
235. Opel, A. Dissertation. Universität Marburg, 1993.
236. Ahlbrecht, H.; Harbach, J.; Hauck, P.; Kalinowski, H.-O. Chem. Ber. 1992, 125, 1753.
237. Rondan, N.G.; Houk, K.N.; Beak, P.; Zajdel, W.J.; Chandrasekhar, J.; Schleyer, P.v.R. J. Org. Chem. 1981, 46, 4108.
238. Marsch, M.; Harms, K.; Zschage, O.; Hoppe, D.; Boche, G. Angew. Chem. 1991, 103, 338; Angew. Chem., Int. Ed. Engl. 1991, 30, 321.
239. Marsch, M.; Harms, K.; Zschage, O.; Hoppe, D.; Boche, G. Angew. Chem. 1991, 103, 338; Angew. Chem., Int. Ed. Engl. 1991, 30, 321.
240. Müller, A.; Marsch, M.; Harms, K.; Lohrenz, J.C.W.; Boche, G. Angew. Chem. 1996, 108, 1639; Angew. Chem., Int. Ed. Engl. 1996, 35, 1518.
241. Müller, A.; Marsch, M.; Harms, K.; Lohrenz, J.C.W.; Boche, G. Angew. Chem. 1996, 108, 1639; Angew. Chem., Int. Ed. Engl. 1996, 35, 1518.
242. Mulliken, R.S. J. Chem. Phys. 1955, 23, 1833.
243. Reed, A.E.; Weinstock, R.B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735.
244. Bader, R.F.W. Chem. Rev. 1991, 91, 893.
245. Seebach, D.; Hansen, J.; Seiler, P.; Gromek, J.M. J. Organomet. Chem. 1985, 285, 1.
246. Brown, K.L.; Damm, L.; Dunitz, J.D.; Eschenmoser, A.; Hobi, R.; Kratky, C. Helv. Chim. Acta 1978, 61, 3108.
247. Boche, G.; Marsch, M.; Harbach, J.; Harms, K.; Ledig, B.; Schubert, F.; Lohrenz, J.C.W.; Ahlbrecht, H. Chem. Ber. 1993, 126. 1887.
248. Sette, F.; Stör, J.; Hitchcock, A.P. J. Chem. Phys. 1984, 81, 4906.
249. Cambridge Structural Database.
250. Ahlbrecht, H.; Boche, G.; Harms, K.; Marsch, M.; Sommer, H. Chem. Ber. 1990, 123, 1853.
251. Enders, D.; Kirchhoff, J.; Gerdes, P.; Mannes, D.; Raabe, G.; Runsink, H.; Boche, G.; Marsch, M.; Ahlbrecht, H.; Sommer, H. Eur. J. Org. Chem. 1998, 63.
252. Bauer, W.; Müller, G.; Pi, R.; Schleyer, P.v.R. Angew. Chem. 1986, 98, 1130; Angew. Chem., Int. Ed. Engl. 1986, 25, 1103.
253. Bauer, W.; Müller, G.; Pi, R.; Schleyer, P.v.R. Angew. Chem. 1986, 98, 1130; Angew. Chem., Int. Ed. Engl. 1986, 25, 1103.
254. Müller, H. Dissertation, Universität Heidelberg, 1964, cited in Hoffmann, R.W. Dehydrobenzen and Cycloalkynes; Verlag Chemie: Weinheim; Academic Press: New York, 1967.
255. Müller, H. Dissertation, Universität Heidelberg, 1964, cited in Hoffmann, R.W. Dehydrobenzen and Cycloalkynes; Verlag Chemie: Weinheim; Academic Press: New York, 1967.
256. Bosold, F.; Zulauf, P.; Marsch, M.; Harms, K.; Lohrenz, J.; Boche; G. Angew. Chem. 1991, 103, 1497; Angew. Chem., Int. Ed. Engl. 1991, 30, 1455.
257. Bosold, F.; Zulauf, P.; Marsch, M.; Harms, K.; Lohrenz, J.; Boche; G. Angew. Chem. 1991, 103, 1497; Angew. Chem., Int. Ed. Engl. 1991, 30, 1455.
258. Amstutz, R.; Schweizer, W.B.; Seebach, D.; Dunitz, J.D. Helv. Chim. Acta 1981, 64, 2617.
259. Pauline, J.A.; Squires, R.R. J. Am. Chem. Soc. 1991, 113, 1845.
260. Hilf, C.; Bosold, F.; Harms, K.; Lohrenz, J.C.W.; Marsch, M.; Schimeczek, M.; Boche, G. Chem. Ber./Recueil 1997, 130, 1201.
261. Hilf, C.; Bosold, F.; Harms, K.; Marsch, M,; Boche, G. Chem. Ber./Recueil 1997, 130, 1213.
262. Boche, G.; Marsch, M.; Müller, A.; Harms, K. Angew. Chem. 1993, 105, 1081; Angew. Chem., Int. Ed. Engl. 1993, 32, 1032.
263. Boche, G.; Marsch, M.; Müller, A.; Harms, K. Angew. Chem. 1993, 105, 1081; Angew. Chem., Int. Ed. Engl. 1993, 32, 1032.
264. Boche, G.; Harms, K.; Marsch, M.; Müller, A. J. Chem. Soc., Chem. Commun. 1994, 1393.
265. Niecke, E.; Becker, P.; Nieger, M.; Stalke, D.; Schoeller, W.W. Angew. Chem. 1995, 107, 2012; Angew. Chem., Int. Ed. Engl. 1995, 34, 1849.
266. Niecke, E.; Becker, P.; Nieger, M.; Stalke, D.; Schoeller, W.W. Angew. Chem. 1995, 107, 2012; Angew. Chem., Int. Ed. Engl. 1995, 34, 1849.
267. Niecke E.; Nieger, M.; Schmidt, O.; Gudat, D.; Schoeller, W.W. J. Am. Chem. Soc. 1999, 121, 519.
268. Hofmann, A.W. Chem. Ber. 1881, 14, 2725.
269. (a) Excellent review on "Rearrangements involving Migration to an Electron-deficient Nitrogen or Oxygen" by Smith, P.A.S. in Molecular Rearrangements; de Mayo, P., Ed.; Vol. 1, Interscience Publ.: New York, 1963; p 457.
270. See also the article on "Base-Catalyzed Rearrangements" by Zimmerman, H.E. in the same volume, p 345.
271. Review acticles (books) on nitrenes: (a) Lwowski, W. Nitrenes; Interscience Publ.: New York, 1970.
272. (b) Lwowski, W. In Reactive Intermediates; Jones, M., Jr.; Moss, R.A., Eds.; Vol. 1, Wiley-Interscience: New York, 1978; p 198.
273. (c) Wentrup, C. In Reactive Intermediates; Abramovich, R.A., Ed.; Plenum Press: New York, 1980; Vol. 1, p 263.
274. (d) Lwowski, W. In Reactive Intermediates; Jones, M., Jr., Moss, R.A., Eds.; John Wiley: New York, 1981; Vol. 2, p 315.
275. (e) Scriven, E.F.V. In Reactive Intermediates; Abramovich, R.A., Ed.; Plenum Press: New York, 1982; Vol. 2, p 1.
276. (f) Lwowski, W. In Reactive Intermediates; Jones, M., Jr., Moss, R.A., Eds.; John Wiley: New York, 1985; Vol. 3, p 306.
277. (g) Edwards, O.E. Uniw. Adama Mickiewicza Poznaniu, Wydz. Mat., Fiz. Chem., [Pr.], Ser. Chem. 1975, 18, 113; Chem. Abstr. 1976, 84, 120633. Although the title Of the article is "Nitrenes and nitrenoids" there is not much on nitrenoids to be found.
278. (g) Edwards, O.E. Uniw. Adama Mickiewicza Poznaniu, Wydz. Mat., Fiz. Chem., [Pr.], Ser. Chem. 1975, 18, 113; Chem. Abstr. 1976, 84, 120633. Although the title Of the article is "Nitrenes and nitrenoids" there is not much on nitrenoids to be found.
279. Lessen, W. Ann. Chem. Pharm. 1872, 161, 347.
280. (a) Stieglitz, J.; Leech, P.N. Chem. Ber. 1913, 46, 2147.
281. (b) Stieglitz, J.; Leech, P.N. J. Am. Chem. Soc. 1914, 36, 272.
282. (c) Vosburgh, I. J. Am. Chem Soc. 1916, 38, 2081.
283. Buck, P.; Köbrich, G. Tetrahedron Lett. 1967, 1563.
284. An excellent review on this topic was written by Erdik, E.; Ay, M. Chem. Rev. 1989, 89, 1947.
285. (a) Coleman, G.H.; Hauser, C.R. J. Am. Chem. Soc. 1928, 50, 1193.
286. (b) Coleman, G.H. J. Am. Chem. Soc. 1933, 55, 3001 and earlier publications cited.
287. Coleman, G.H.; Hermanson, J.L.; Johnson, H.L. J. Am. Chem. Soc. 1937, 59, 1896.
288. (a) Schewerdina, N.I.; Kotscheschkow, K.A. J. Gen. Chem. USSR (Engl. Transl.) 1938, 8, 1825; Chem. Zentralbl. 1940, 1, 360.
289. (a) Schewerdina, N.I.; Kotscheschkow, K.A. J. Gen. Chem. USSR (Engl. Transl.) 1938, 8, 1825; Chem. Zentralbl. 1940, 1, 360.
290. (b) Schewerdina, N.I.; Kotscheschkow, K.A. Chem. Zentralbl. 1942, 1, 1872.
291. See also (c) Gilman, H.; Swayampati, D.R. J. Am. Chem. Soc. 1957, 79, 208 and earlier work cited.
292. (d) Erdik, E. Commun. Fac. Sci. Univ. Ankara Ser. B. 1980, 26, 83; Chem. Abstr. 1981, 95, 115634p. For structurally related nitrenoids.
293. (d) Erdik, E. Commun. Fac. Sci. Univ. Ankara Ser. B. 1980, 26, 83; Chem. Abstr. 1981, 95, 115634p. For structurally related nitrenoids.
294. (e) Kreher, R.; Bauer, A.; Hennige, H.Z. Naturforsch. 1974, 29b, 231.
295. (f) Basha, A.; Brooks, D.W. J. Chem. Soc., Chem. Commun. 1987, 305.
296. (a) Wakefield, B.J. The Chemistry of Organolithium Compounds; Pergamon Press: Oxford, 1974; p 161.
297. (b) Lit. cit., p 215.
298. (c) Beak, P.; Basha, A.; Kokko, B. J. Org. Chem. 1982, 47, 2822.
299. (d) Beak, P.; Kokko, B.J. Tetrahedron Lett. 1983, 24, 561.
300. (a) Beak, P.; Basha, A.; Kokko, B. J. Am. Chem. Soc. 1984, 106, 1511.
301. Beak, P.; Basha, A.; Kokko, B.; Leo, D. J. Am. Chem. Soc. 1986, 108, 6016.
302. (a) Sheradsky, T.; Nir, Z. Tetrahedron Lett. 1969, 77 and earlier papers cited.
303. (b) Radhakrishna, A.S.; Loudon, G.M.; Miller, M.J. J. Org. Chem. 1979, 44, 4836.
304. (a) Taylor, E.C.; Sun, J.H. Synthesis 1980, 801.
305. (b) Scopes, D.I.C.; Kluge, A.F.; Edwards, J.A. J. Org. Chem. 1977, 42, 376.
306. (c) Tamura, Y.; Minamikawa, J.; Ikeda, M. Synthesis 1977, 1.
307. (a) Colvin, E.W.; Kirby, G.W.; Wilson A.C. Tetrahedron Lett. 1982, 23, 3835.
308. (b) Boche, G.; Bernheim, M.; Schrott, W. Tetrahedron Lett. 1982, 23, 5399.
309. (a) Müller, E.; Disselhoff, H. Naturwissenschaften 1933, 21, 661.
310. (b) Müller, E.; Disselhoff, H. Liebigs Ann. Chem. 1934, 521, 250.
311. (c) Müller, E.; Kreutzmann, W. Liebigs Ann. Chem. 1934, 521, 264.
312. (d) Müller, E.; Ludsteck, D. Chem. Ber. 1955, 88, 921.
313. (e) Müller, E.; Rundel, W. Chem. Ber. 1956, 89, 1065.
314. (f) Beutler, R.; Zeeh, B.; Müller, E. Chem. Ber. 1969, 102, 2636.
315. Boche, G.; Lohrenz, J.C.W.; Schubert, F. Tetrahedron 1994, 50, 5889.
316. Review: Campbell, M.M.; Johnson, G. Chem. Rev. 1978, 78, 65.
317. Raper, H.S. Report to British Chemical War Department, May 1917; Chem. Abstr. 1922, 16, 28559.
318. Raper, H.S. Report to British Chemical War Department, May 1917; Chem. Abstr. 1922, 16, 28559.
319. Sharpless, K.B.; Hori, T.; Truesdale, L.K.; Dietrich, C.O. J. Am. Chem. Soc. 1976, 98, 269.
320. Sharpless, K.B.; Chong, A.O.; Oshima, K. J. Org. Chem. 1976, 41, 177.
321. Rudolph, J.; Sennhenn, P.C.; Vlaar, C.P.; Sharpless, K.B. Angew. Chem. 1996, 108, 2991; Angew. Chem., Int. Ed. Engl. 1996, 35, 2995.
322. Rudolph, J.; Sennhenn, P.C.; Vlaar, C.P.; Sharpless, K.B. Angew. Chem. 1996, 108, 2991; Angew. Chem., Int. Ed. Engl. 1996, 35, 2995.
323. Bruncko, M.; Schlingloff, G.; Sharpless, K.B. Angew. Chem. 1997, 109, 1580; Angew. Chem., Int. Ed. Engl. 1997, 36, 1583.
324. Bruncko, M.; Schlingloff, G.; Sharpless, K.B. Angew. Chem. 1997, 109, 1580; Angew. Chem., Int. Ed. Engl. 1997, 36, 1583.
325. Jeong, J.U.; Tao, B.; Sagasser, I., Henniges, H.; Sharpless, K.B. J. Am. Chem. Soc. 1998, 120, 6844.
326. Tomooka, C.S.; Le Cloux, D.D.; Sasaki, H.; Carreira, E.M. Org. Lett. 1999, 1, 149.
327. Genet; J.P.; Mallart, S.; Greck, C.; Piveteau, E. Tetrahedron Lett. 1991, 32, 2359.
328. Genet, J.P.; Hajicek, J.; Bischoff, L.; Greck, C. Tetrahedron Lett. 1992, 33, 2677.
329. Review articles: (a) Pelter, A.; Smith, K. In Comprehensive Organic Chemistry; Barton, D.R.H., Ollis, W.D., Eds.; Pergamon Press: Oxford, 1979; Vol. 3, p 687.
330. (b) Pelter, A.; Smith, K.; Brown, H.C. Boran Reagents; Academic Press: London, 1988.
331. (c) Suzuki, A.; Dhillon, R.S. Top. Curr. Chem. 1986, 130, 23. For further lit., see ref 171. Recent publications.
332. (d) Fernandez, E.; Hooper, M.W.; Knight, F.I.; Brown, J.M. Chem. Commun. 1997, 173.
333. (e) Knight, F.I.; Brown, J.M.; Lazzari, D.; Ricci, A.; Blacker, A.J. Tetrahedron 1997, 53, 11411.
334. West, R.; Boudjouk, P. J. Am. Chem. Soc. 1973, 95, 3987.
335. Casarini, A.; Dembech, P.; Lazzari, D.; Marini, E.; Reginato, G.; Ricci, A.; Seconi, G. J. Org. Chem. 1993, 58, 5620.
336. Boche, G.; Meier, C.; Kleemiss, W. Tetrahedron Lett. 1988, 29, 1777.
337. Bosold, F.; Boche, G.; Kleemiss, W. Tetrahedron Lett. 1988, 29, 1781.
338. Wilkie, C.A.; Dimmel, D.R. J. Am. Chem. Soc. 1972, 94, 8600.
339. Boche, G.; Wagner, H.-U. Chem. Commun. 1984, 1591.
340. (a) Armstrong, D.R.; Snaith, R.; Walker, G.T. Chem. Commun. 1985, 789.
341. 2NOLi, see Armstrong, D.R.; Clegg, W.; Hodgson, S.M.; Snaith, R.; Wheatley, A.E.H. J. Organomet. Chem. 1998, 550, 233.
342. McKee, M.L. J. Am. Chem. Soc. 1985, 107, 859.
343. Sun, H.-B.; Wang, X.-D.; Liu, C.-B.; Deng, C.-H. Huaxue Xuebao 1997, 55, 250; Chem. Abstr. 1997, 126, 347552 (without mentioning any of the earlier quantum-chemical publications on nitrenoids).
344. Sun, H.-B.; Wang, X.-D.; Liu, C.-B.; Deng, C.-H. Huaxue Xuebao 1997, 55, 250; Chem. Abstr. 1997, 126, 347552 (without mentioning any of the earlier quantum-chemical publications on nitrenoids).
345. Olmstead, M.M.; Power, P.P. Inorg. Chem. 1986, 25, 4057.
346. Boche, G.; Bole, C.; Bosold, F.; Harms, K.; Marsch, M. Angew. Chem. 1994, 106, 90; Angew. Chem., Int. Ed. Engl. 1994, 33, 115.
347. Boche, G.; Bole, C.; Bosold, F.; Harms, K.; Marsch, M. Angew. Chem. 1994, 106, 90; Angew. Chem., Int. Ed. Engl. 1994, 33, 115.
348. Bosold, F.; Zulauf, P.; Marsch, M.; Harms, K.; Lohrenz, J.C.W.; Boche, G. Angew. Chem. 1991, 103, 1497; Angew. Chem., Int. Ed. Engl. 1991, 30, 1455.
349. Bosold, F.; Zulauf, P.; Marsch, M.; Harms, K.; Lohrenz, J.C.W.; Boche, G. Angew. Chem. 1991, 103, 1497; Angew. Chem., Int. Ed. Engl. 1991, 30, 1455.
350. Seebach, D.; Amstutz, R.; Laube, T.; Schweizer, W.B.; Dunitz, J.D. J. Am. Chem. Soc. 1985, 107, 5403.
351. Hamilton, G.A. J. Am. Chem. Soc. 1964, 86, 3391.
352. Some examples are listed in the following. (a) Cytochrome P-450 dependent monooxygenase enzyme system: Fish, R.H.; Kimmel, E.C.; Casida, J.E. J. Organomet. Chem. 1976, 118, 41.
353. (b) S-Oxygenation and O-demethylation with cytochrome P-450: Watanabe, Y.; Oae, S.; Iyanagi, T. Bull. Chem. Soc. Jpn. 1982, 55, 188.
354. (c) Sulfoxide to sulfone oxidation by cytochrome P-450: Watanabe, Y.; Iyanagi, T.; Oar, S. Tetrahedron Lett. 1982, 23, 533.
355. + and cytochrome P-450: Shaik, S.; Filatov, M.; Schröder, D.; Schwarz, H. Chem. Eur. J. 1998, 4, 193. Reviews: McMurry, T.J.; Groves, J.T. In Cytochrome P-450: Structure, Mechanism and Biochemistry; Ortiz de Montellano, R.R. Plenum Press: New York, 1985; Chapter 1. Metalloporphyrin catalyzed oxidation; Montanari, F., Casella, L., Eds.; Kluwer Academic Publishers: Dordrecht, 1994.
356. + and cytochrome P-450: Shaik, S.; Filatov, M.; Schröder, D.; Schwarz, H. Chem. Eur. J. 1998, 4, 193. Reviews: McMurry, T.J.; Groves, J.T. In Cytochrome P-450: Structure, Mechanism and Biochemistry; Ortiz de Montellano, R.R. Plenum Press: New York, 1985; Chapter 1. Metalloporphyrin catalyzed oxidation; Montanari, F., Casella, L., Eds.; Kluwer Academic Publishers: Dordrecht, 1994.
357. + and cytochrome P-450: Shaik, S.; Filatov, M.; Schröder, D.; Schwarz, H. Chem. Eur. J. 1998, 4, 193. Reviews: McMurry, T.J.; Groves, J.T. In Cytochrome P-450: Structure, Mechanism and Biochemistry; Ortiz de Montellano, R.R. Plenum Press: New York, 1985; Chapter 1. Metalloporphyrin catalyzed oxidation; Montanari, F., Casella, L., Eds.; Kluwer Academic Publishers: Dordrecht, 1994.
358. (e) Tetrahydropterin and dihydroflavin-dependent monooxygenases: Dmitrienko, G.I.; Snieckus, V.; Viswanatha, T. Bioorg. Chem. 1977, 6, 421.
359. (f) Oxygenase reactions: Visser, C.M. Biorg. Chem. 1980, 9, 261.
360. (g) p-Hydroxybenzoate hydroxylase: Husain, M.; Entsch, B.; Ballou, D.P.; Massey, V.; Chapman, P.J. J. Biol. Chem. 1980, 255, 4189.
361. Flavin-dependent hydroxylation: Visser, C.M. Eur. J. Biochem. 1983, 135, 543; Naturwisschenschaften 1983, 70, 412.
362. Flavin-dependent hydroxylation: Visser, C.M. Eur. J. Biochem. 1983, 135, 543; Naturwisschenschaften 1983, 70, 412.
363. (i) Carbonyl oxides: Kumar, S.; Murray, R.W. Tetrahedron Lett. 1980, 21, 4781.
364. (j) Dioxirane or carbonyl oxide: Tezuka, T.; Iwaki, M. Tetrahedron Lett. 1983, 24, 3109.
365. (k) Dimethyldioxirane: Bravo, A.; Fontana, F.; Frenza, G.; Minisci, F.; Zhao, L. J. Org. Chem. 1998, 63, 254. Review: Adam, W.; Hadjiarapoglou, L.P. Top. Curr. Chem. 1993, 49, 2227.
366. (k) Dimethyldioxirane: Bravo, A.; Fontana, F.; Frenza, G.; Minisci, F.; Zhao, L. J. Org. Chem. 1998, 63, 254. Review: Adam, W.; Hadjiarapoglou, L.P. Top. Curr. Chem. 1993, 49, 2227.
367. (l) Oxyfunctionalization with Methyl(trifluoromethyl)-dioxirane: Mello, R,; Fiorentino, M.; Fusco, C.; Curci, R. J. Am. Chem. Soc. 1989, 111, 6749.
368. (m) Oxidation of alkanes and alcohols with aromatic peracids: Bravo, A.; Fontana, F.; Minisci, F.; Serri, A. Chem. Commun. 1996, 1843.
369. (n) Vanadium (v) peroxo complexes: Mimoun, H.; Saussine, L.; Daire, E.; Postel, M.; Fischer, J.; Weiss, R. J. Am. Chem. Soc. 1983, 105, 3101.
370. III catalase model: Barton, D.H.R.; Hu, B. Tetrahedron 1996, 52, 10313. Review on Gif systems: Barton, D.H.R.; Doller, D. Acc. Chem. Res. 1992, 25, 504.
371. III catalase model: Barton, D.H.R.; Hu, B. Tetrahedron 1996, 52, 10313. Review on Gif systems: Barton, D.H.R.; Doller, D. Acc. Chem. Res. 1992, 25, 504.
372. (p) Photolysis of aromatic sulfoxides: Wan, Z.; Jenks, W.S. J. Am. Chem. Soc. 1995, 117, 2667.
373. (a) Julia, M.; Saint-Jalmes, V.P.; Verpeaux, J.-N. Synlett 1993, 233.
374. (b) Chemla, F.; Julia, M.; Uguen, D. Bull. Soc. Chim. Fr. 1994, 131, 639.
375. (c) Julia, M.; Saint-Jalmes, V.P.; Pit, K.; Verpeaux, J.-N.; in part Hollingworth, G. Bull. Soc. Chim. Fr. 1996, 133, 15.
376. Boche, G.; Bosold, F.; Lohrenz, J.C.W. Angew. Chem. 1994, 106, 1228; Angew. Chem., Int. Ed. Engl. 1994, 33, 1161.
377. Boche, G.; Bosold, F.; Lohrenz, J.C.W. Angew. Chem. 1994, 106, 1228; Angew. Chem., Int. Ed. Engl. 1994, 33, 1161.
378. Frankland, E. Liebigs Ann. Chem. 1853, 85, 329.
379. Meyer, V.; Demuth, R. Ber. Dtsch. Chem. Ges. 1890, 23, 394.
380. Klement, I.; Knochel, P. Synlett 1995, 1113.
381. Reviews comprising the "autoxidation side reaction" of RMgX and RLi spezies: (a) Sosnovsky, G.; Brown, J.H. Chem. Rev. 1966, 66, 529.
382. (b) Maher-Detweiler, M. Methoden Org. Chem. (Houben-Weyl) 4th ed., Vol. E13, 1988; part 1, p 176.
383. (c) Schöllkopf, U. Methoden Org. Chem. (Houben-Weyl) Vol. 13/1, 1970; p 170.
384. (d) Nützel, K. Methoden Org. Chem. (Houben-Weyl), Vol. 13/2a, 1973; p 234.
385. (e) Wedemeyer, K.-F. Methoden Org. Chem. (Houben-Weyl) Vol. 6/1c, 1976; part 1, p 141.
386. (f) Geibel, K.; Hofmann, H.; Kropf, H.; Thiem, J. Methoden Org. Chem. (Houben Weyl) Vol. 6/1a, 1979; part 1, p 217.
387. (g) Nützel, K. Methoden Org. Chem. (Houben-Weyl) Vol. 13/2a, 1973; p 700.
388. (h) Nützel, K. Methoden Org. Chem. (Houben-Weyl) Vol. 13/2a, 1973; p 908.
389. Bodroux, M.F. Bull. Soc. Chim. 1904, 31, 35.
390. (a) Wuyts, H. Compt. Rend. 1909, 148, 930.
391. (b) Wuyts, H. Bull. Soc. Chim. Belg. 1927, 36, 222.
392. Porter, C.W.; Steel, C. J. Am. Chem. Soc. 1920, 42, 2650.
393. Grignard, V.; Lepayre, L. Bull. Soc. Chim. Fr. 1928, 43, 141; ibid. 930.
394. Grignard, V.; Lepayre, L. Bull. Soc. Chim. Fr. 1928, 43, 141; ibid. 930.
395. Walling, C.; Buckler, S.A. J. Am. Chem. Soc. 1955, 77, 6032.
396. Lawesson, S.-O.; Yang, N.C. J. Am. Chem. Soc. 1959, 81, 4230.
397. Müller, E.; Töpel, T. Chem. Ber. 1939, 72, 273.
398. (a) Piacenza, G.; Riccola, S.; Contos, N. Acta Toxicol. Ther. 1998, 19, 1.
399. (b) Moskalink, K.; Katovic, D. Tekstil 1997, 46, 139.
400. (c) Rocha Gonzalves, A.M.A.; Pereira, M.M. J. Mol. Catal. A: Chem. 1996, 113, 209 and further lit. cit.
401. (d) Zhang, W.; Loebach, J.L.; Wilson, S.R.; Jacobsen, E.N. J. Am. Chem. Soc. 1990, 112, 2801.
402. (e) Palucki, M.; Pospisil, P.J.; Zhang, W.; Jacobsen, E.N. J. Am. Chem. Soc. 1994, 116, 9333.
403. (f) Irie, R.; Noda, K.; Ito, Y.; Matsumoto, N.; Katsuki, T. Tetrahedron Lett. 1990, 31, 7345.
404. (g) Ito, Y.N.; Katsuki, T. Bull. Chem. Soc. Jpn. 1999, 72, 603.
405. 2O without bond lengths and angles was published by Fehér, F.; Hirschfeld, D.; Linke, K.-H. Acta Crystallogr. 1962, 15, 1188.
406. (i) Becker, H.G.O. J. Prakt. Chem. 1995, 337, 690.
407. Warner, P.; Lu, S.-L. J. Org. Chem. 1976, 41, 1459.
408. (a) Panek, E.J.; Kaiser, L.R.; Whitesides, G.M. J. Am. Chem. Soc. 1977, 99, 3708.
409. (b) Neumann, H.; Seebach, D. Chem. Ber. 1978, 111, 2782 also used oxenoids LiOOR to oxidize vinyl-lithium compounds.
410. Other oxidations of aryl-metal compounds: (a) Nilsson, M.; North, T. Acta Chem. Scand. 1963, 17, 1157.
411. (b) Kemp, M.S.; Burden, R.S.; Loeffler, R.S.T. J. Chem. Soc., Perkin Trans 1 1983, 2267.
412. (c) The oxidation of aryllithium and aryl-Grignard compounds with 2-tert-butylperoxy-1,3,2-dioxaborolane was performed by Hoffmann, R.W.; Ditrich, K. Synthesis 1983, 107.
413. Husemann, M. Ph.D. thesis, Universität Marburg, 1996.
414. Whitesides, G.M.; SanFilippo, J., Jr.; Casey, C.P.; Panek, E.J. J. Am. Chem. Soc. 1967, 89, 5302. The yields which were reported by the authors are as follows: 333 (84%), 334 (14%), and 335 (5%). Since this adds up to 103%, we have deducted 1% from each number.
415. (a) Lipshutz, B.H.; Siegmann, K.; Garda, E.; Kayser, F. J. Am. Chem. Soc. 1993, 115, 9276.
416. See also (b) Camus, A.; Marsich, N. J. Organomet. Chem. 1972, 46, 385.
417. (c) Lambert, G.J.; Duffley, R.P.; Dalzell, H.C.; Razdan, R.K. J. Org. Chem. 1982, 47, 3350.
418. (a) Möller, M.; Husemann, M.; Boche, G. J. Organomet. Chem., in print.
419. 4, respectively, Hoffmann, R.W.; Hölzer, B.; Knopff, O.; Harms, K. Angew. Chem. 2000, 112, 3206; Angew. Chem., Int. Ed. Engl. 2000, 39, 3072, observed partial racemization in the resultant alcohol.
420. 4, respectively, Hoffmann, R.W.; Hölzer, B.; Knopff, O.; Harms, K. Angew. Chem. 2000, 112, 3206; Angew. Chem., Int. Ed. Engl. 2000, 39, 3072, observed partial racemization in the resultant alcohol.
421. (a) Williams, I.D.; Pedersen, S.F.; Sharpless, K.B.; Lippard, S.J. J. Am. Chem. Soc. 1984, 106, 6430.
422. (b) Pedersen, S.F.; Dewan, J.C.; Eckman, R.R.; Sharpless, K.B. J. Am. Chem. 1987, 109, 1279.
423. (c) Woodard, S.S.; Finn, M.G.; Sharpless, K.B. J. Am. Chem. Soc. 1991, 113, 106.
424. (d) Finn, M.G.; Sharpless, K.B. J. Am. Chem. Soc. 1991, 113, 113 and earlier lit. cited.
425. Corey, E.J. J. Org. Chem. 1990, 55, 1693.
426. (a) Pitchen, P.; Kagan, H.B. Tetrahedron Lett. 1984, 25, 1049.
427. (b) Girard, C.; Kagan, H.B. Angew. Chem. 1998, 110, 3088; Angew. Chem., Int. Ed. Engl. 1998, 37, 2922. This review article summarizes the publications of H.B. Kagan on this topic, for further reactions of this type.
428. (b) Girard, C.; Kagan, H.B. Angew. Chem. 1998, 110, 3088; Angew. Chem., Int. Ed. Engl. 1998, 37, 2922. This review article summarizes the publications of H.B. Kagan on this topic, for further reactions of this type.
429. see: (c) Bonchio, M.; Calloni, S.; DiFuria, F.; Licini, G.; Modena, G.; Moro, S.; Nugent, W.A. J. Am. Chem. Soc. 1997, 119, 6935 cit. lit.
430. (d) Komatsu, N.; Hashizume, M.; Sugita, T.; Uemura, S. J. Org. Chem. 1993, 58, 4529.
431. Schulz, M.; Kluge, R.; Schüssler, M.; Hoffmann, G. Tetrahedron 1995, 51, 3175.
432. (a) Adam, W.; Peters, K.; Renz, M. J. Org. Chem. 1997, 62, 3183.
433. See also (b) Adam, W.; Richter, M. J. Acc. Chem. Res. 1994, 27, 57.
434. 3TiOOR.0 It rather results from the preparation of 356.
435. (a) Schmiedeberg, N. Diploma thesis, Universität Marburg, 1997; the luminescence-time diagrams were made in cooperation with Dr. K. Böhme and Professor H.-D. Brauer, Institut für Physikalische und Theoretische Chemie, Universität Frankfurt am Main.
436. (a) Schmiedeberg, N. Diploma thesis, Universität Marburg, 1997; the luminescence-time diagrams were made in cooperation with Dr. K. Böhme and Professor H.-D. Brauer, Institut für Physikalische und Theoretische Chemie, Universität Frankfurt am Main.
437. see also (b) Böhme, K.; Brauer, H.-D. Inorg. Chem. 1992, 31, 3468.
438. (a) Hamann, J.J.; Dahlmann, J.; Höft, E. Oxid. Commun. 1980, 1, 183.
439. (b) Hamann, J.J.; Höft, E.; Dahlmann, J.; Ivanov, S.K. Oxid. Commun. 1981, 2, 127.
440. (c) Ivanov, S.K.; Kateva, J. Oxid. Commun. 1983, 5, 367.
441. (a) Aubry, J.M. J. Am. Chem. Soc. 1985, 107, 5844.
442. (b) Aubry, J.M.; Carin, B. Inorg. Chem. 1988, 27, 2013.
443. (c) Aubry, J.M.; Cazin, B.; Duprat, F. J. Org. Chem. 1989, 54, 726.
444. (d) Nardello, V.; Briviba, K.; Sies, H.; Aubry, J.-M. Chem. Commun. 1998, 599.
445. (a) Ball, R.E.; Edwards, J.O.; Haggett, M.L.; Jones, P. J. Am. Chem. Soc. 1967, 89, 2331.
446. (b) Evans, D.F.; Upton, M.W. J. Chem. Soc., Dalton Trans. 1985, 1151.
447. (c) Goodman, J.F.; Robson, P. J. Chem. Soc. 1963, 2871.
448. (d) Koubek, E.; Welsch, J.E. J. Org. Chem. 1968, 33, 445, and earlier lit.
449. (e) See also ref 216b.
450. Reviews: (a) Simandi, L.I. Catalytic Activation of Dioxygen by Metal Complexes; Kluwer Publ.: Dordrecht, 1992.
451. (b) Strukul, G. Catalytic Oxidations with Hydrogen Peroxide as Oxidant; Kluwer Publ.: Dordrecht, 1992.
452. (c) Curci, R.; Edwards, J.O. In Organic Peroxides; Swern, D., Ed.; Wiley-Interscience: New York, 1970; Vol. 1, p 199.
453. (d) Sheldon, R.A. In The Chemistry of Peroxides; Patai, S., Ed.; John Wiley & Sons: Chichester, 1983; p 173.
454. (e) Howard, J.A. In The Chemistry of Peroxides; Patai, S., Ed.; John Wiley & Sons: Chichester 1983; p 251.
455. (a) Sokolov, A.; Chetyrbrok, L.N.; Shushunov, V.A. Zh. Obsch. Khimii 1963, 33, 2027.
456. (b) Belyaev, V.A.; Nemtsov, M.S. Zh. Obsch. Khimii 1961, 31, 3861.
457. Ball, D.L.; Edwards, J.O. J. Am. Chem. Soc. 1956, 78, 1125.
458. 219a,c,dc220c.
459. Corey, E.J.; Mehrotra, M.M.; Khan, A.U. J. Am. Chem. Soc. 1986, 108, 2472.
460. (a) Cerkovnik, J.; Plesnicar, B. J. Am. Chem. Soc. 1993, 115, 12169.
461. (b) Plesnicar, B.; Cerkovnik, J:; Keller, J.; Kovac, F. J. Am. Chem. Soc. 1991, 113, 4946.
462. Shell Oil, Eng. Patent 1, 249, 079, 1971; Chem. Abstr. 1971, 74, 12981m.
463. Shell Oil, Eng. Patent 1, 249, 079, 1971; Chem. Abstr. 1971, 74, 12981m.
464. Adam, W.; Kumar, R.; Reddy, T.I.; Renz, M. Angew. Chem. 1996, 108, 944; Angew. Chem. Int. Ed. Engl. 1996, 35, 880.
465. Adam, W.; Kumar, R.; Reddy, T.I.; Renz, M. Angew. Chem. 1996, 108, 944; Angew. Chem. Int. Ed. Engl. 1996, 35, 880.
466. (a) Jørgensen, K.A. Chem. Rev. 1989, 89, 431. This is an excellent review on "Transition Metal Catalyzed Epoxidation" with special emphasis on the theoretical treatment of the reactions.
467. see also: (b) Sheldon, R.A.; Kochi, J.A. Metal-Catalyzed Oxidations of Organic Compounds; Academic Press: New York, 1981, and ref. cited.
468. (c) Schröder, D.; Schalley, C.A.; Schwarz, H. In Deutsche Forschungsgemeinschaft, Peroxide Chemistry, Mechanistic and Preparative Aspects of Oxygen Transfer Adam, W., Ed.; Wiley VCH: New York, 2000; p 639.
469. Ikegami, S.; Katsuki, T.; Yamaguchi, M. Chem. Lett. 1987, 83.
470. (a) Lubben, T.V.; Wolczanski, P.T. J. Am. Chem. Soc. 1987, 109, 424.
471. (b) Blackburn, T.F.; Labinger, J.A.; Schwartz, J. Tetrahedron Lett. 1975, 3041.
472. Brindley, P.B.; Scotton, M.J. J. Chem. Soc., Perkin Trans 2 1981, 419.
473. (a) Davidson, P.J.; Lappert, M.F.; Pearce, R. J. Organomet. Chem. 1973, 57, 269.
474. (b) Brindley, P.B.; Hodgson J.C. J. Organomet. Chem. 1974, 65, 57.
475. (a) Krohn, K.; Vinke, I.; Adam, H. J. Org. Chem. 1996, 61, 1467.
476. (b) Krohn, K.; Khanbabaee, K.; Rieger, H. Chem. Ber. 1990, 123, 1357.
477. (a) Sharpless, K.B.; Michaelson, R.C. J. Am. Chem. Soc. 1973, 95, 6136.
478. (b) Chong, A.O.; Sharpless, K.B. J. Org. Chem. 1977, 42, 1587.
479. Mimoun, H.; Chaumette, P.; Saussine, L.; Fischer, J.; Mitschler, A. J. Organomet. Chem. 1983, 250, 291.
480. (a) Mihelich, E.D. Tetrahedron Lett. 1979, 4729.
481. (b) Mihelich, E.D.; Daniels, K.; Eickhoff, D.J. J. Am. Chem. Soc. 1981, 103, 7690.
482. Itoh, T.; Jitsukawa, K.; Kaneda, K.; Teranishi, S. J. Am. Chem. Soc. 1979, 101, 159.
483. Laszlo, P.; Levart, M.; Singh, G.P.; Tetrahedron Lett. 1991, 32, 3167.
484. (a) Kollar, J. US Patent 3350422, 1967, and 3351635, 1967.
485. (b) Mimoun, H. Angew. Chem. 1982, 94, 750; Angew. Chem., Int. Ed. Engl. 1982, 21, 734.
486. (b) Mimoun, H. Angew. Chem. 1982, 94, 750; Angew. Chem., Int. Ed. Engl. 1982, 21, 734.
487. (c) Mimoun, H. In Comprehensive Coordination Chemistry; Wilkinson, G., Gillard, R., McCleverty, J.A., Eds.; Pergamon Press: New York, 1987; Vol. 6, p 327, cit. lit.
488. (a) Thiel, W.R.; Priermeier, T. Angew. Chem. 1995, 107, 1870; Angew. Chem., Int. Ed. Engl. 1995, 34, 1737.
489. (a) Thiel, W.R.; Priermeier, T. Angew. Chem. 1995, 107, 1870; Angew. Chem., Int. Ed. Engl. 1995, 34, 1737.
490. (b) Thiel, W.R. Chem. Ber. 1996, 129, 575.
491. (c) Thiel W.R.; Eppinger, J. Chem. Eur. J. 1997, 3, 696.
492. Wahl, G.; Kleinhenz, D.; Schorm, A.; Sundermeyer, J.; Stowasser, R.; Rummey, C.; Bringmann, G.; Fickert, C.; Kiefer, W. Chem. Eur. J. 1999, 5, 3237.
493. Machii, K.; Watanabe, Y.; Morishima, I. J. Am. Chem. Soc. 1995, 117, 6691, and earlier relevent work cited.
494. (a) Bold, M. Ph.D. thesis in progress, Universität Marburg, 2000.
495. (b) Lubben, M.; Meetsma, A.; Wilkinson, E.C.; Feringa, B.; Que, L., Jr. Angew. Chem. 1995, 107, 1610; Angew. Chem., Int. Ed. Engl. 1995, 34, 1512.
496. (b) Lubben, M.; Meetsma, A.; Wilkinson, E.C.; Feringa, B.; Que, L., Jr. Angew. Chem. 1995, 107, 1610; Angew. Chem., Int. Ed. Engl. 1995, 34, 1512.
497. (c) Ménage, S.; Wilkinson, E.C.; Que, L., Jr.; Fontecave, M. Angew. Chem. 1995, 107, 198; Angew. Chem., Int. Ed. Engl. 1995, 34, 203.
498. (c) Ménage, S.; Wilkinson, E.C.; Que, L., Jr.; Fontecave, M. Angew. Chem. 1995, 107, 198; Angew. Chem., Int. Ed. Engl. 1995, 34, 203.
499. (d) Kim, J.; Larka, E.; Wilkinson, E.C.; Que, L., Jr. Angew. Chem. 1995, 107, 2191; Angew. Chem., Int. Ed. Engl. 1995, 34, 2048.
500. (d) Kim, J.; Larka, E.; Wilkinson, E.C.; Que, L., Jr. Angew. Chem. 1995, 107, 2191; Angew. Chem., Int. Ed. Engl. 1995, 34, 2048.
501. (e) Nam, W.; Lim, M.H.; Moon, S.K.; Kim, C. J. Am. Chem. Soc. 2000, 122, 10805.
502. (f) Nam, W.; Lim, M.H.; Lee, H.J.; Kim, C. J. Am. Chem. Soc. 2000, 122, 6641, and earlier references cited.
503. Bach, R.D.; Su, M.-D.; Andres, J.L.; Schlegel, H.B. J. Am. Chem. Soc. 1993, 115, 8763.
504. Jørgensen, K.A. J. Chem. Soc., Perkin Trans. 2 1994, 117.
505. Bach, R.D.; Wolber, G.J.; Coddens, B.A. J. Am. Chem. Soc. 1984, 106, 6098.
506. Boche, G.; Möbus, K.; Harms, K.; Lohrenz, J.C.W.; Marsch, M. Chem. Eur. J. 1996, 2, 604.
507. Schalley, C.A.; Schröder, D.; Schwarz, H.; Möbus, K.; Boche, G. Chem. Ber./Recueil 1997, 130, 1085.
508. (a) Lias, S.G.; Bartmess, J.E.; Liebman, J.F.; Holmes, J.L.; Levin, R.D.; Mallard, W.G. Gas-Phase Ion and Neutral Thermochemistry. J. Phys. Chem. Rev. Data 1988, Suppl. 1.
509. (b) Lias, S.G.; Liebman, J.F.; Levin, R.D.; Kafafi, S.A. NIST Standard Reference Database, Position Ion Energetics, Version 2.01, Gaithersburg, MD, 1994, cit. lit.
510. Jørgensen, K.A.; Wheeler, R.A.; Hoffmann, R. J. Am. Chem. Soc. 1987, 109, 3240.
511. Finn, M.G.; Sharpless, K.B. In Asymmetric Synthesis; Morrison, J.D., Ed.; Academic Press: New York, 1985; Vol. 5, p 247.
512. (a) Wu, Y.-D.; Lai, D.K.W. J. Am. Chem. Soc. 1995, 117, 11327.
513. Wu, Y.-D.; Lai, D.K.W. J. Org. Chem. 1995, 60, 673.
514. Tantanak, D.; Vincent, M.A.; Hillier, I.H. Chem. Commun. 1998, 1031.
515. (a) Adam, W.; Corma, A.; Reddy, T.I.; Renz, M. J. Org. Chem. 1997, 62, 3631.
516. (b) Clerici, M.G.; Ingallina, P. J. Catal. 1993, 140, 71.
517. Boche, G.; Möbus, K.; Harms, K.; Marsch, M. J. Am. Chem. Soc. 1996, 118, 2770.
518. Van Asselt, A.; Santarsiero, B.D.; Bercaw, J.E. J. Am. Chem. Soc. 1986, 108, 8291.
519. Mimoun, H.; Chaumette, P.; Mignard, M.; Saussine, L.; Fischer, J.; Weiss, R. Neuv. J. Chim. 1983, 7, 467.
520. (a) Tamao, K.; Kawachi, A. Angew. Chem. 1995, 107, 886; Angew. Chem., Int. Ed. Engl. 1995, 34, 818.
521. (a) Tamao, K.; Kawachi, A. Angew. Chem. 1995, 107, 886; Angew. Chem., Int. Ed. Engl. 1995, 34, 818.
522. (b) Tamao, K.; Kawachi, A. Organometallics 1995, 14, 3108.
523. (c) Kawachi, A.; Tamao, K. Organometallics 1996, 15, 4653.
524. (d) Kawachi, A.; Tamao, K. Bull. Chem. Soc. Jpn. 1997, 70, 945.
525. (e) Tananka, Y.; Hada, M.; Kawachi, A.; Tamao, K.; Nakatsuji, H. Organometallics 1998, 17, 4573.
526. (f) Tamao, K.; Asahara, M.; Saeki, T.; Toshimitu, A. Angew. Chem. 1999, 111, 3520; Angew. Chem., Int. Ed. 1999, 38, 3316.
527. (f) Tamao, K.; Asahara, M.; Saeki, T.; Toshimitu, A. Angew. Chem. 1999, 111, 3520; Angew. Chem., Int. Ed. 1999, 38, 3316.