Thermodynamic scales for sulfur atom transfer and oxo-for-sulfido exchange reactions

Chemical Reviews

Volumn 106, Issue 11, 2006, Pages 4747-4783

  Donahue, James P ^a  

^a Tulane University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ATOMS; ENTHALPY; OXIDATION; SULFUR; SYNTHESIS (CHEMICAL);

EXCHANGE REACTIONS; SULFUR ATOM TRANSFER; THERMODYNAMIC SCALES;

THERMODYNAMICS;

EID: 33751441094     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr050044w     Document Type: Review

References (356)

1. (a) Griffith, W. P. Coord. Chem. Rev. 1970, 5, 459.
2. (b) Holm, R. H. Chem. Rev. 1987, 87, 1401.
3. (c) Herrmann, W. A.; Herdtweck, E.; Flöbel, M.; Kulpe, J.; Küsthardt, U.; Okuda, J. Polyhedron 1987, 6, 1165.
4. (d) Nugent, W. A.; Mayer, J. M. Metal-Ligand Multiple Bonds; Wiley: New York, 1988.
5. (e) Bottomley, F. Polyhedron 1992, 11, 1707.
6. (f) Woo, L. K. Chem. Rev. 1993, 93, 1125.
7. (g) Mehrotra, R. C.; Singh, A. Chem. Soc. Rev. 1996, 25, 1.
8. Müller, P.; Fruit, C. Chem. Rev. 2003, 103, 2905.
9. (a) Adam, W.; Bargon, R. M. Chem. Commun. 2001, 1910.
10. (b) Adam, W.; Bargon, R. M.; Schenk, W. A. J. Am. Chem. Soc. 2003, 125, 3871.
11. (c) Adam, W.; Bargon, R. M. Chem. Rev. 2004, 104, 251.
12. Adam, W.; Bargon, R. M.; Bosio, S. G.; Schenk, W. A.; Stalke, D. J. Org. Chem. 2002, 67, 7037.
13. For representative examples of olefin epoxidation by transition metal oxo complexes, see: (a) Groves, J. T.; Quinn, R. J. Am. Chem. Soc. 1985, 107, 5790.
14. (b) Samsel, E. G.; Srinivasan, K.; Kochi, J. K. J. Am. Chem. Soc. 1985, 107, 7606.
15. (c) Collman, J. P.; Kodadek, T.; Raybuck, S. A.; Brauman, J. I.; Papazian, L. M. J. Am. Chem. Soc. 1985, 107, 4343.
16. (d) Bailey, C. L.; Drago, R. S. J. Chem. Soc., Chem. Commun. 1987, 179.
17. (e) Rajapakse, N.; James, B. R.; Dolphin, D. Selective Oxidations Catalyzed by Dioxo(porphyrinato)ruthenium(VI) Species. In New Developments in Selective Oxidation; Centi, G., Trifiró, F., Eds.; Elsevier: Amsterdam, The Netherlands, 1990; pp 109-117.
18. (f) Jacobsen, E. N.; Zhang, W.; Muci, A. R.; Ecker, J. R.; Deng, L. J. Am. Chem. Soc. 1991, 113, 7063.
19. (g) Bailey, A. J.; Griffith, W. P.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1994, 1833.
20. (h) Brandes, B. D.; Jacobsen, E. N. Tetrahedron Lett. 1995, 36, 5123.
21. (i) Al-Ajlouni, A. M.; Espenson, J. H. J. Org. Chem. 1996, 61, 3969.
22. (j) Copéret, C.; Adolfsson, H.; Sharpless, K. B. Chem. Commun. 1997, 1565.
23. (a) Hille, R. Chem. Rev. 1996, 96, 2757.
24. (b) Huber, R.; Hof, P.; Duarte, R. O.; Moura, J. J. G.; Moura, I.; Liu, M.-Y.; LeGall, J.; Hille, R.; Archer, M.; Romão, M. J. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 8846.
25. (c) Romão, M. J.; Huber, R. Struct. Bonding 1998, 90, 69.
26. (d) Enroth, C.; Eger, B. T.; Okamoto, K.; Nishino, T.; Nishino, T.; Pai, E. F. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 10723.
27. (a) Massey, V.; Edmondson, D. J. Biol. Chem. 1970, 245, 6595.
28. (b) Wahl, R. C.; Rajagopalan, K. V. J. Biol. Chem. 1982, 257, 1354.
29. (a) Nagarajan, K.; Joshi, H. K.; Chaudbury, P. K.; Pal, K.; Cooney, J. J. A.; Enemark, J. H.; Sarkar, S. Inorg. Chem. 2004, 43, 4532.
30. (b) Prisner, T.; Lyubenova, S.; Atabay, Y.; MacMillan, F.; Kröger, A.; Klimmek, O. J. Biol. Inorg. Chem. 2003, 8, 419.
31. (a) Chan, M. K.; Mukund, S.; Kletzin, A.; Adams, M. W. W.; Rees, D. C. Science 1995, 267, 1463.
32. (b) Johnson, M. K.; Rees, D. C.; Adams, M. W. W. Chem. Rev. 1996, 96, 2817.
33. (c) Hu, Y.; Faham, S.; Roy, R.; Adams, M. W. W.; Rees, D. C. J. Mol. Biol. 1999, 286, 899.
34. (d) Raaijmakers, H.; Macieira, S.; Dias, J. M.; Teixeira, S.; Bursakov, S.; Huber, R.; Moura, J. J. G.; Moura, I.; Romão, M. J. Structure 2002, 10, 1261.
35. (a) Ploegman, J. H.; Drent, G.; Kalk, K. H.; Hol, W. G. J. J. Mol. Biol. 1979, 127, 149.
36. (b) Bordo, D.; Deriu, D.; Colnaghi, R.; Carpen, A.; Pagani, S.; Bolognesi, M. J. Mol. Biol. 2000, 298, 691.
37. (c) Bordo, D.; Bork, P. EMBO Reports 2002, 3, 741.
38. (a) Westley, J.; Adler, H.; Westley, L.; Nishida, C. Fundam. Appl. Toxicol. 1983, 3, 377.
39. (b) Huxtable, R. J. Biochemistry of Sulfur; Plenum: New York, 1986; pp 124-129.
40. (c) Nagahara, N.; Ito, T.; Minami, M. Histol. Histopathol. 1999, 14, 1277.
41. (a) Alexander, K.; Volini, M. J. Biol. Chem. 1987, 262, 6595.
42. (b) Mihara, H.; Esaki, N. Appl. Microbiol. Biotechnol. 2002, 60, 12.
43. (c) Saidu, Y. Afr. J. Biotechnol. 2004, 3, 370.
44. (a) Gates, B. C.; Katzer, J. R.; Schuit, G. C. A. Hydrodesulfurization. In Chemistry of Catalytic Processes; McGraw-Hill: New York, 1979; pp 390-447.
45. (b) Prins, R.; de Beer, V. H. J.; Somorjai, G. A. Catal. Rev. - Sci. Eng. 1989, 31, 1.
46. (c) Angelici, R. J. Hydrodesulfurization and Hydrodenitrogenation. In Encyclopedia of Inorganic Chemistry; King, R. B., Ed.; Wiley: New York, 1994; Vol. 3, pp 1433-1443.
47. (d) Sánchez-Delgado, R. A. J. Mol. Catal. 1994, 86, 287.
48. (e) Angelici, R. J. Bull. Soc. Chim. Belg. 1995, 104, 265.
49. (f) Bianchim, C.; Meli, A. J. Chem. Soc., Dalton Trans. 1996, 801.
50. (g) Angelici, R. J. Polyhedron 1997, 16, 3073.
51. (h) Bianchini, C.; Meli, A. Acc. Chem. Res. 1998, 31, 109.
52. (i) Babich, I. V.; Moulijn, J. A. Fuel 2003, 82, 607.
53. (j) Breysse, M.; Djega-Mariadassou, G.; Pessayre, S.; Geantet, C.; Vrinat, M.; Pérot, G.; Lemaire, M. Catal. Today 2003, 84, 129.
54. (k) Bianchini, C.; Meli, A.; Vizza, F. J. Organomet. Chem. 2004, 689, 4277.
55. (a) Angelici, R. J. Acc. Chem. Res. 1988, 21, 387.
56. (b) Choi, M.-G.; Daniels, L. M.; Angelici, R. J. Inorg. Chem. 1991, 30, 3647.
57. (a) Friend, C. M.; Roberts, J. T. Acc. Chem. Res. 1988, 21, 394.
58. (b) Liu, A. C.; Friend, C. M. J. Am. Chem. Soc. 1991, 113, 820.
59. (c) Wiegand, B. C.; Friend, C. M. Chem. Rev. 1992, 92, 491.
60. Gabay, J.; Dietz, S.; Bernatis, P.; Rakowski Dubois, M. Organometallics 1993, 12, 3630.
61. (a) Stirling, D. The Sulfur Problem: Cleaning up Industrial Feedstocks; Royal Society of Chemistry: Cambridge, U.K., 2000.
62. (b) U.S. Environmental Protection Agency Clean Air Act Tier 2; 1999.
63. (a) Parks, C. R.; Parker, D. K.; Chalfant, H. J. Prepr. Am. Chem. Soc., Div. Pet. Chem. 1974, 19, 325.
64. (b) Coran, A. Y. CHEMTECH 1983, 13, 106.
65. (c) Krejsa, M. R.; Koenig, J. L. Rubber Chem. Technol. 1993, 66, 376.
66. (d) Ignatz-Hoover, F. Rubber World 1999, 220, 24.
67. (e) Nieuwenhuizen, P. J. CATTECH 2000, 3, 184.
68. Holm, R. H.; Donahue, J. P. Polyhedron 1993, 12, 571.
69. (a) Diemann, E.; Müller, A. Coord. Chem. Rev. 1973, 10, 79.
70. (b) Vahrenkamp, H. Angew. Chem., Int. Ed. Engl. 1975, 14, 322.
71. (c) Rice, D. A. Coord. Chem. Rev. 1978, 25, 199.
72. (d) Müller, A.; Diemann, E.; Jostes, R.; Bögge, H. Angew. Chem., Int. Ed. Engl. 1981, 20, 934.
73. (e) Herrmann, W. A. Angew. Chem., Int. Ed. Engl. 1986, 25, 56.
74. (f) Müller, A.; Diemann, E. Sulfides. In Comprehensive Coordination Chemistry; Wilkinson, G., Gillard, R. D., McCleverty, J. A., Eds.; Pergamon: Oxford, U.K., 1987; Vol. 2, pp 515-550.
75. (g) Trnka, T. M.; Parkin, G. Polyhedron 1997, 16, 1031.
76. (h) Kuchta, M. C.; Parkin, G. Coord. Chem. Rev. 1998, 176, 323.
77. (i) Parkin, G. Prog. Inorg. Chem. 1998, 47, 1.
78. (j) Rauchfuss, T. B. Inorg. Chem. 2004, 43, 14.
79. Capps, K. B.; Wixmerten, B.; Bauer, A.; Hoff, C. D. Inorg. Chem. 1998, 37, 2861.
80. Goddard, C. A.; Holm, R. H. Inorg. Chem. 1999, 38, 5389.
81. Lundmark, P. J.; Kubas, G. J.; Scott, B. L. Organometallics 1996, 15, 3631.
82. Pawlicki, S. H.; Noll, B. C.; Kanney, J. A.; Rakowski Dubois, M. Inorg. Chem. 2003, 42, 1556.
83. (a) Blower, P. J.; Dilworth, J. R.; Hutchinson, J. P.; Nicholson, T.; Zubieta, J. J. Chem. Soc., Dalton Trans. 1986, 1339.
84. (b) Gilletti, P. F.; Femec, D. A.; Keen, F. I.; Brown, T. M. Inorg. Chem. 1992, 31, 4008.
85. fH°(298) for S(g), none of which would produce any significant differences in the tables of thermodynamic data presented in this paper. The number cited and its uncertainty are obtained from the National Institute of Standards website: http://webbook.nist.gov/ chemistry/.
86. 2 Organic Substances in SI Units; Lide, Jr., D. R., Ed.; American Chemical Society and the American Institute of Physics: Washington, DC; J. Phys. Chem. Ref. Data 1982 11 (Suppl. 2).
87. Binnewies, M.; Milke, E. Thermochemical Data of Elements and Compounds; Wiley-VCH: Weinheim, Germany, 2002.
88. Cox, J. D.; Pilcher, G. Thermochemistry of Organic and Organometallic Compounds; Academic Press: New York, 1970.
89. Pedley, J. B.; Naylor, R. D.; Kirby, S. P. Thermochemical Data of Organic Compounds, 2nd ed.; Chapman and Hall: New York, 1986.
90. NIST-JANAF Thermochemical Tables, 4th ed.; Chase, Jr., M. W., Ed.; American Chemical Society and the American Institute of Physics: Washington, DC; J. Phys. Chem. Ref. Data 1998, Monograph 9.
91. Standard Potentials in Aqueous Solution; Bard, A. J., Parsons, P., Jordan, J., Eds.; Marcel Dekker: New York, 1985.
92. Mills, K. C. Thermodynamic Data for Inorganic Sulphides, Selenides and Tellurides; Butterworth: London, U.K., 1974.
93. Barin, I. Thermochemical Data of Pure Substances; VCH: Weinheim, Germany, 1993.
94. Benson, S. W. Chem. Rev. 1978, 78, 23.
95. Kirklin, D. R.; Domalski, E. S. J. Chem. Thermodyn. 1988, 20, 743.
96. Kirklin, D. R.; Chickos, J. S.; Liebman, J. F. Struct. Chem. 1996, 7, 355.
97. Deniz, A. A.; Peters, K. S.; Snyder, G. J. Science 1999, 286, 1119.
98. Dittmer, G.; Niemann, U. Philips J. Res. 1982, 37, 1.
99. Huang, J.; Schanz, H.-J.; Stevens, E. D.; Nolan, S. P.; Capps, K. B.; Bauer, A.; Hoff, C. D. Inorg. Chem. 2000, 39, 1042.
100. (a) Pearson, R. G. J. Am. Chem. Soc. 1963, 85, 3533.
101. (b) Pearson, R. G. Science 1966, 151, 172.
102. (c) Pearson, R. G. Chem. Br. 1967, 3, 103.
103. (d) Pearson, R. G. Inorg. Chim. Acta 1995, 240, 93.
104. Ghanty, T. K.; Ghosh, S. K. J. Phys. Chem. 1993, 97, 4951.
105. Ibdah, A.; Espenson, J. H.; Jenks, W. S. Inorg. Chem. 2005, 44, 8426.
106. (a) Chernick, C. L.; Pedley, J. B.; Skinner, H. A. J. Chem. Soc. 1957, 1851.
107. (b) Hartley, S. B.; Holmes, W. S.; Jacques, J. K.; Mole, M. F.; McCoubrey, J. C. Q. Rev. Chem. Soc. 1963, 17, 204.
108. Johnson, A. R.; Davis, W. M.; Cummins, C. C.; Serron, S.; Nolan, S. P.; Musaev, D. G.; Morokuma, K. J. Am. Chem. Soc. 1998, 120, 2071.
109. (a) Hall, K. A.; Mayer, J. M. J. Am. Chem. Soc. 1992, 114, 10402.
110. (b) Hall, K. A.; Mayer, J. M. Inorg. Chem. 1994, 33, 3289.
111. (a) Rabinovich, D.; Parkin, G. J. Am. Chem. Soc. 1991, 113, 5904.
112. (b) Rabinovich, D.; Parkin, G. Inorg. Chem. 1995, 34, 6341.
113. (a) Vogel, E.; Klärmer, F.-G. Angew. Chem., Int. Ed. Engl. 1968, 7, 374.
114. (b) Boyd, D. R.; Jerina, D. M.; Daly, J. W. J. Org. Chem. 1970, 35, 3170.
115. (c) Akhtar, M. N.; Boyd, D. R.; Hamilton, J. G. J. Chem. Soc., Perkin Trans. 1 1979, 2437.
116. (a) Cortez, C.; Harvey, R. G.; Jackson, J.; Chapman, O. L. Org. Synth. 1978, 58, 12.
117. (b) Mello, R.; Ciminale, F.; Fiorentino, M.; Fusco, C.; Prencipe, T.; Curci, R. Tetrahedron Lett. 1990, 31, 6097.
118. Murray, R. W.; Singh, M.; Rath, N. P. Struct. Chem. 1999, 10, 419.
119. Rozen, S.; Bareket, Y.; Blum, J. Tetrahedron Lett. 1997, 38, 2333.
120. Rebelo, S. L. H.; Simões, M. M. Q.; Neves, M. Graca P. M. S.; Silva, A. M. S.; Cavaleiro, J. A. S. Chem. Commun. 2004, 608.
121. (a) Reinecke, M. G.; Del Mazza, D.; Obeng, M. J. Org. Chem. 2003, 68, 70.
122. (b) Reinecke, M. G.; Del Mazza, D. J. Org. Chem. 1989, 54, 2142.
123. (c) Del Mazza, D.; Reinecke, M. G. J. Org. Chem. 1988, 53, 5799.
124. (d) Callander, D. D.; Coe, P. L.; Tatlow, J. C. Chem. Commun. 1966, 143.
125. (a) Bartlett, P. D.; Roderick, W. R.; Andersen, W. C. Inorg. Synth. 1966, 8, 100.
126. (b) Mäusle, H.-J.; Steudel, R. Z. Anorg. Allg. Chem. 1980, 463, 27.
127. (c) Donohue, J.; Caron, A.; Goldish, E. J. Am. Chem. Soc. 1961, 83, 3748.
128. (d) Steidel, J.; Pickardt, J.; Steudel, R. Z. Naturforsch., B: Chem. Sci. 1978, 33, 1554.
129. (a) Schmidt, M.; Block, B.; Block, H. D.; Köpf, H.; Wilhelm, E. Angew. Chem., Int. Ed. Engl. 1998, 7, 632.
130. (b) Kawada, I.; Hellner, E. Angew. Chem., Int. Ed. Engl. 1970, 9, 379.
131. (c) Steudel, R.; Reinhardt, R.; Schuster, F. Angew. Chem., Int. Ed. Engl. 1977, 16, 715.
132. (d) Steudel, R.; Steidel, J.; Pickardt, J.; Schuster, F.; Reinhardt, R. Z. Naturforsch., B: Chem. Sci. 1980, 35, 1378.
133. (e) Steudel, R.; Mäusle, H.-J. Z. Anorg. Allg. Chem. 1981, 478, 156.
134. (a) Schmidt, M.; Wilhelm, E. Chem. Commun. 1970, 1111.
135. (b) Steudel, R.; Bergemann, K.; Buschmann, J.; Luger, P. Inorg. Chem. 1996, 35, 2184.
136. (a) Steudel, R.; Steidel, J.; Sandow, T.; Schuster, F. Z. Naturforsch., B: Chem. Sci. 1978, 33, 1198.
137. (b) Reinhardt, R.; Steudel, R.; Schuster, F. Angew. Chem., Int. Ed. Engl. 1978, 17, 57.
138. (c) Steudel, R.; Steidel, J.; Reinhardt, R. Z. Naturforsch., B: Chem. Sci. 1983, 38, 1548.
139. (a) Steidel, J.; Steudel, R. J. Chem. Soc., Chem Commun. 1982, 1312.
140. (b) Sandow, T.; Steidel, J.; Steudel, R. Angew. Chem., Int. Ed. Engl. 1982, 21, 794.
141. (c) Steudel, R.; Steidel, J.; Sandow, T. Z. Naturforsch., B: Chem. Sci. 1986, 41, 958.
142. (a) Schmidt, M.; Wilhelm, E. Angew. Chem., Int. Ed. Engl. 1966, 5,
143. (b) Kutoglu, A.; Hellner, E. Angew. Chem., Int. Ed. Engl. 1966, 5, 965.
144. (c) Schmidt, M.; Knippschild, G.; Wilhelm, E. Chem. Ber. 1968, 101, 381.
145. (d) Steudel, R.; Mäusle, H.-J. Angew. Chem., Int. Ed. Engl. 1979, 18, 152.
146. (e) Steidel, J.; Steudel, R.; Kutoglu, A. Z. Anorg. Allg. Chem. 1981, 476, 171.
147. Steudel, R.; Schumann, O.; Buschmann, J.; Luger, P. Angew. Chem., Int. Ed. Engl. 1998, 37, 2377.
148. Strauss, R.; Steudel, R. Z. Naturforsch., B: Chem. Sci. 1988, 43, 1151.
149. (a) Schmidt, M.; Wilhelm, E.; Debaerdemaeker, T.; Hellner, E.; Kutoglu, A. Z. Anorg. Allg. Chem. 1974, 405, 153.
150. (b) Debaerdemaeker, T.; Kutoglu, A. Naturwissenschaften 1973, 60, 49.
151. (c) Debaerdemaeker, T.; Kutoglu, A. Cryst. Struct. Commun. 1974, 3, 611.
152. (a) Debaerdemaeker, T.; Hellner, E.; Kutoglu, A.; Schmidt, M.; Wilhelm, E. Naturwissenschaften 1973, 60, 300.
153. (b) Steudel, R.; Strauss, R. J. Chem. Soc., Dalton Trans. 1984, 1775.
154. Tebbe, F. N.; Wasserman, E.; Peet, W. G.; Vatvars, A.; Hayman, A. C. J. Am. Chem. Soc. 1982, 104, 4971.
155. (a) Bartlett, P. D.; Cox, E. F.; Davis, R. E. J. Am. Chem. Soc. 1961, 83, 103.
156. (b) Fehér, F.; Kurz, D. Z. Naturforsch., B: Chem. Sci. 1969, 24, 1089.
157. Heymann, D.; Bachilo, S. M.; Weisman, R. B.; Marriott, T.; Cataldo, F. Fullerenes, Nanotubes, Carbon Nanostruct. 2002, 10, 37.
158. (a) Carlsen, L.; Harrit, N.; Holm, A. J. Chem. Soc., Perkin Trans. 1 1976, 1404.
159. (b) Karlström, G.; Roos, B. O.; Carlsen, L. J. Am. Chem. Soc. 1984, 106, 1557.
160. (a) Snyder, J. P. J. Am. Chem. Soc. 1974, 96, 5005.
161. (b) Carlsen, L.; Holm, A.; Koch, E.; Stilkerieg, B. Acta Chem. Scand. 1977, B31, 679.
162. (a) Bonini, B. F.; Maccagnani, G.; Mazzanti, G. J. Chem. Soc., Chem. Commun. 1976, 431.
163. (b) Rindorf, G.; Carlsen, L. Acta Crystallogr., Sect. B 1979, 35, 1179.
164. (c) Le Nocher, A. M.; Metzner, P. Tetrahedron Lett. 1991, 32, 747.
165. (d) Huang, R.; Espenson, J. H. J. Org. Chem. 1999, 64, 6935.
166. Adam, W.; Deeg, O.; Weinkötz, S. J. Org. Chem. 1997, 62, 7084.
167. Adam, W.; Weinkötz, S. J. Am. Chem. Soc. 1998, 120, 4861.
168. (a) Huisgen, R.; Rapp, J. J. Am. Chem. Soc. 1987, 109, 902.
169. (b) Ishii, A.; Hoshino, M.; Nakayama, J. Pure Appl. Chem. 1996, 68, 869.
170. (c) Huisgen, R.; Rapp, J. Tetrahedron 1997, 53, 939.
171. Nakayama, J.; Ishii, A. Adv. Heterocycl. Chem. 2000, 77, 221.
172. (a) Ishii, A.; Akazawa, T.; Maruta, T.; Nakayama, J.; Hoshino, M.; Shiro, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 777.
173. (b) Ishii, A.; Jin, Y.-N.; Nagaya, H.; Hoshino, M.; Nakayama, J. Tetrahedron Lett. 1995, 36, 1867.
174. (c) Ishii, A.; Umezawa, K.; Nakayama, J. Tetrahedron Lett. 1997, 38, 1431.
175. (d) Ishii, A.; Yamashita, R.; Saito, M.; Nakayama, J. J. Org. Chem. 2003, 68, 1555.
176. Shimada, K.; Kodaki, K.; Aoyagi, S.; Takikawa, Y.; Kabuto, C. Chem. Lett. 1999, 695.
177. Wieringa, J. H.; Wynberg, H.; Strating, J. Tetrahedron Lett. 1972, 13, 2071.
178. Wieringa, J. H.; Wynberg, H.; Strating, J. Tetrahedron 1974, 30, 3053.
179. Ishii, A.; Kawai, T.; Tekura, K.; Oshida, H.; Nakayama, J. Angew. Chem., Int. Ed. Engl. 2001, 40, 1924.
180. Baechler, R. D.; Stack, M.; Stevenson, K.; Vanvalkenburgh, V. Phosphorus Sulfur Silicon Relat. Elem. 1990, 48, 49.
181. Nowottnick, H.; Blachnik, R. Z. Anorg. Allg. Chem. 1999, 625, 1966.
182. Jason, M. E. Inorg. Chem. 1997, 36, 2641.
183. Shindo, M.; Matsumura, Y.; Okawara, R. J. Organomet. Chem. 1968, 11, 299.
184. Zingaro, R. A.; Merijanian, A. J. Organomet. Chem. 1964, 1, 369.
185. Otera, J.; Kadowaki, T.; Okawara, R. J. Organomet. Chem. 1969, 19, 213.
186. Bhattacharya, S. N.; Saxena, A. K. Ind. J. Chem., Sect. A 1979, 17, 307.
187. Raj, P.; Saxena, A. K.; Singhal, K.; Ranjan, A. Polyhedron 1985, 4, 251.
188. 3 is available from Strem Chemicals, Pfaltz & Bauer, and Gelest, Inc.
189. 3 itself as a ligand coordinated to the metal through the sulfur atom. The identity of these complexes has not been established, as they have been characterized only by IR spectroscopy. See: Mikulski, C. M.; Karayannis, N. M. Inorg. Chim. Acta 1983, 77, L43.
190. 3: Capozzi, G.; Menichetti, S.; Ricci, A.; Taddei, M. J. Organomet. Chem. 1988, 344, 285.
191. 3: Hänssgen, D.; Reuter, P.; Döllen, G. J. Organomet. Chem. 1986, 317, 159.
192. Batchelor, R. J.; Einstein, F. W. B.; Jones, C. H. W.; Sharma, R. D. Inorg. Chem. 1988, 27, 4636.
193. 3: Steliou, K.; Mrani, M. J. Am. Chem. Soc. 1982, 104, 3104.
194. 3: Glidewell, C.; Liles, D. C. J. Organomet. Chem. 1981, 224, 237.
195. 3: Kerschl, S.; Wrackmeyer, B.; Männig, D.; Nöth, H.; Staudigl, R. Z. Naturforsch., B: Chem. Sci. 1987, 42, 387.
196. Sampson, M. L.; Richardson, J. F.; Noble, M. E. Inorg. Chem. 1992, 31, 2726.
197. Gingras, M.; Harpp, D. N. Tetrahedron Lett. 1990, 31, 1397.
198. Harpp, D. N.; Gingras, M. Tetrahedron Lett. 1987, 28, 4373.
199. Harpp, D. N.; Gingras, M.; Aida, T.; Chan, T. H. Synthesis 1987, 1122.
200. Cowley, A. J. Chem. Educ. 1964, 41, 530.
201. Handbook of Preparative Inorganic Chemistry; Brauer, G., Ed.; Academic Press: New York, 1963; Vol. 1.
202. (a) Leung, Y. C.; Waser, J.; van Houten, S.; Vos, A.; Wiegers, G. A.; Wiebenga, E. H. Acta Crystallogr. 1957, 10, 574.
203. (b) Chattopadhyay, T. K.; May, W.; von Schnering, H. G.; Pawley, G. S. Z. Kristallogr. 1983, 165, 47.
204. Vos, A.; Olthof, R.; van Bolhuis, F.; Botterweg, R. Acta Crystallogr. 1965, 19, 864.
205. Dixon, D. T.; Einstein, F. W. B.; Penfold, B. R. Acta Crystallogr. 1965, 18, 221.
206. Blachnik, R.; Matthiesen, J.; Müller, A.; Nowottnik, H.; Reuter, H. Z. Kristallogr. 1998, 213, 233.
207. Blachnik, R.; Peukert, U.; Czediwoda, A.; Engelen, B.; Boldt, K. Z. Anorg. Allg. Chem. 1995, 621, 1637.
208. van Houten, S.; Wiebenga, E. H. Acta Crystallogr. 1957, 10, 156.
209. Perkins, P. G. Inorg. Chim. Acta 1983, 73, 45.
210. Meisel, M.; Grunze, H. Z. Anorg. Allg. Chem. 1970, 373, 265.
211. Nowottnik, H.; Blachnik, R. Z. Anorg. Allg. Chem. 2000, 626, 611.
212. Barieux, J.-J.; Démarcq, M. C. J. Chem. Soc., Chem. Commun. 1982, 176.
213. Bjorholm, T.; Jakobsen, H. J. J. Am. Chem. Soc. 1991, 113, 27.
214. Bues, W.; Somer, M.; Brockner, W. Z. Anorg. Allg. Chem. 1981, 476, 153.
215. Griffin, A. M.; Minshall, P. C.; Sheldrick, G. M. J. Chem. Soc., Chem. Commun. 1976, 809.
216. 6 appears to be available only from the Aldrich Chemical Co.
217. (a) Leandri, G.; Rebora, P. Experientia 1957, 13, 71.
218. (b) Leandri, G.; Rebora, P. Gazz. Chim. Ital. 1957, 87, 503.
219. (c) Leandri, G.; Spinelli, D. Ann. Chim. 1959, 49, 1689.
220. (d) Foffani, A.; Leandri, G.; Zanon, I.; Carpanelli, C. Tetrahedron Lett. 1959, 1 (11), 21.
221. (e) Jannelli, L.; Sciacovelli, O.; Carpanelli, C. Ann. Chim. 1963, 53, 1541.
222. Leandri, G.; Busetti, V.; Valle, G.; Mammi, M. Chem. Commun. 1970, 413.
223. Bindra, A. P.; Elix, J. A.; Morris, G. C. Aust. J. Chem. 1969, 22, 2483.
224. For the preparation and crystal structure of mercury(II) acetamide, see: Kamenar, B.; Grdenić, D. Inorg. Chim. Acta 1969, 3, 25.
225. Cramer, R. J. Org. Chem. 1961, 26, 3476.
226. The best pricing for phenyl N-sulfinylamine is from TCI America.
227. Al-Ajely, M. S.; Al-Rawi, J. M. A.; Elvidge, J. A. J. Chem. Soc., Perkin Trans. 1 1982, 1575.
228. Goehring, M.; Weis, G. Angew. Chem. 1956, 68, 678.
229. (a) Pandey, K. K.; Nigam, H. L. Rev. Inorg. Chem. 1984, 6, 69.
230. (b) Pandey, K. K. Coord. Chem. Rev. 1995, 140, 37.
231. Gaffney, T. R.; Ibers, J. A. Inorg. Chem. 1982, 21, 2851.
232. Werner, H.; Kolb, O. Angew. Chem., Int. Ed. Engl. 1979, 18, 865.
233. Gaffney, T. R.; Ibers, J. A. Inorg. Chem. 1982, 21, 2860.
234. Baird, M. C.; Wilkinson, G. J. Chem. Soc. A 1967, 865.
235. Skapski, A. C.; Troughton, P. G. H. Chem. Commun. 1969, 170.
236. Bryan, J. C.; Geib, S. J.; Rheingold, A. L.; Mayer, J. M. J. Am. Chem. Soc. 1987, 109, 2826.
237. Su, F.-M.; Bryan, J. C.; Jang, S.; Mayer, J. M. Polyhedron 1989, 8, 1261.
238. Berg, D. J.; Burns, C. J.; Andersen, R. A.; Zalkin, A. Organometallics 1989, 8, 1865.
239. Avens, L. R.; Barnhart, D. M.; Burns, C. J.; McKee, S. D.; Smith, W. H. Inorg. Chem. 1994, 33, 4245.
240. (a) Ferm, R. J. Chem. Rev. 1957, 57, 621.
241. (b) Neels, J.; Meisel, M.; Moll, R. Z. Chem. 1984, 24, 389.
242. (c) Mizuno, T.; Nishiguchi, I.; Hirashima, T.; Sonoda, N. Heteroat. Chem. 1990, 1, 157.
243. Lorber, C.; Donahue, J. P.; Goddard, C. A.; Nordlander, E.; Holm, R. H. J. Am. Chem. Soc. 1998, 120, 8102.
244. Sung, K.-M.; Holm, R. H. Inorg. Chem. 2001, 40, 4518.
245. Jiang, J.; Holm, R. H. Inorg. Chem. 2004, 43, 1302.
246. Cotton, F. A.; Schmid, G. Inorg. Chem. 1997, 36, 2267.
247. (a) Coucouvanis, D.; Hadjikyriacou, A. Inorg. Chem. 1986, 25, 4317.
248. (b) Hadjikyriacou, A. I.; Coucouvanis, D. Inorg. Chem. 1987, 26, 2400.
249. Halbert, T. R.; McGauley, K.; Pan, W.-H.; Czernuszewicz, R. S.; Stiefel, E. I. J. Am. Chem. Soc. 1984, 106, 1849.
250. (a) Sullivan, A. B.; Boustany, K. Int. J. Sulfur Chem. A. 1971, 1, 207.
251. (b) Coucouvanis, D.; Kanatzidis, M.; Simhon, E.; Baenziger, N. C. J. Am. Chem. Soc. 1982, 104, 1874.
252. (c) Hou, Y.; Abu-Yousef, I. A.; Doung, Y.; Harpp, D. N. Tetrahedron Lett. 2001, 42, 8607.
253. Murphy, V. J.; Parkin, G. J. Am. Chem. Soc. 1995, 117, 3522.
254. Howard, W. A.; Trnka, T. M.; Waters, M.; Parkin, G. J. Organomet. Chem. 1997, 528, 95.
255. Howard, W. A.; Parkin, G. Organometallics 1993, 12, 2363.
256. Bottomley, F.; Drummond, D. F.; Egharevba, G. O.; White, P. S. Organometallics 1986, 5, 1620.
257. Beckhaus, R.; Thiele, K.-H. Z. Anorg. Allg. Chem. 1989, 573, 195.
258. Balch, A. L.; Benner, L. S.; Olmstead, M. M. Inorg. Chem. 1979, 18, 2996.
259. (a) Lee, C.-L.; Besenyei, G.; James, B. R.; Nelson, D. A.; Lilga, M. A. J. Chem. Soc., Chem. Commun. 1985, 1175.
260. (b) Besenyei, G.; Lee, C.-L.; Gulinski, J.; Rettig, S. J.; James, B. R.; Nelson, D. A.; Lilga, M. A. Inorg. Chem. 1987, 26, 3622.
261. (c) Barnabas, A. F.; Sallin, D.; James, B. R. Can. J. Chem. 1989, 67, 2009.
262. (d) Wong, T. Y. H.; Barnabas, A. F.; Sallin, D.; James, B. R. Inorg. Chem. 1995, 34, 2278.
263. (a) Heyke, O.; Hiller, W.; Lorenz, I.-P. Chem. Ber. 1991, 124, 2217.
264. (b) Heyke, O.; Beuter, G.; Lorenz, I.-P. Z. Naturforsch., B: Chem. Sci. 1992, 47, 668.
265. Kuncheria, J.; Mirza, H. A.; Jenkins, H. A.; Vittal, J. J.; Puddephatt, R. J. J. Chem. Soc., Dalton Trans. 1998, 285.
266. Antonelli, D. M.; Cowie, M. Inorg. Chem. 1990, 29, 3339.
267. McDonald, R.; Cowie, M. Inorg. Chem. 1993, 32, 1671.
268. Bianchini, C.; Mealli, C.; Meli, A.; Sabat, M. Inorg. Chem. 1986, 25, 4617.
269. Reich, P.; Martin, D. Chem. Ber. 1965, 98, 2063.
270. Martin, D. Chem. Ber. 1964, 97, 2689.
271. (a) Wentrup, C.; Kambouris, P. Chem. Rev. 1991, 91, 363.
272. (b) Wentrup, C.; Flammang, R. J. Phys. Org. Chem. 1998, 11, 350.
273. Adam, W.; Bargon, R. M. Eur. J. Org. Chem. 2001, 1959.
274. Yu, Z.-X.; Wu, Y.-D. J. Org. Chem. 2003, 68, 6049.
275. Jensen, K. A.; Holm, A.; Huge-Jensen, E. Acta Chem. Scand. 1969, 23, 2919.
276. (a) Lieber, E.; Pillai, C. N.; Ramachandran, J.; Hites, R. D. J. Org. Chem. 1957, 22, 1750.
277. (b) Lieber, E.; Oftedahl, E.; Rao, C. N. R. J. Org. Chem. 1963, 28, 194.
278. (c) Kirmse, W. Chem. Ber. 1960, 93, 2353.
279. (d) Jensen, K. A.; Pedersen, C. Adv. Heterocycl. Chem. 1964, 3, 263.
280. (e) Jensen, K. A.; Holm, A.; Pedersen, C. T. Acta Chem. Scand. 1964, 18, 566.
281. (f) Ikeda, S.; Murai, T.; Ishihara, H.; Kato, S. Synthesis 1990, 415.
282. Preuss, F.; Noichl, H. Z. Naturforsch., B: Chem. Sci. 1987, 42, 121.
283. Partyka, D. V.; Staples, R. J.; Holm, R. H. Inorg. Chem. 2003, 42, 7877.
284. (a) Cherkasov, R. A.; Kutyrev, G. A.; Pudovik, A. N. Tetrahedron 1985, 41, 2567.
285. (b) Cava, M. P.; Levinson, M. I. Tetrahedron 1985, 41, 5061.
286. (c) Jesberger, M.; Davis, T. P.; Barner, L. Synthesis 2003, 1929.
287. (a) Callahan, K. P.; Durand, P. J.; Rieger, P. H. J. Chem. Soc., Chem. Commun. 1980, 75.
288. (b) Callahan, K. P.; Durand, P. J. Inorg. Chem. 1980, 19, 3211.
289. Sato, M.; Miller, K. M.; Enemark, J. H.; Strouse, C. E.; Callahan, K. P. Inorg. Chem. 1981, 20, 3571.
290. Young, C. G.; Enemark, J. H.; Collison, D.; Mabbs, F. E. Inorg. Chem. 1987, 26, 2925.
291. (a) Duatti, A.; Tisato, F.; Refosco, F.; Mazzi, U.; Nicolini, M. Inorg. Chem. 1989, 28, 4564.
292. (b) Tisato, F.; Bolzati, C.; Duatti, A.; Bandoli, G.; Refosco, F. Inorg. Chem. 1993, 32, 2042.
293. Tahmassebi, S. K.; Mayer, J. M. Organometallics 1995, 14, 1039.
294. Yan, X. F.; Fox, B. L.; Tiekink, E. R. T.; Young, C. G. J. Chem. Soc., Dalton Trans. 1994, 1765.
295. Young, C. G.; Roberts, S. A.; Ortega, R. B.; Enemark, J. H. J. Am. Chem. Soc. 1987, 109, 2938.
296. Young, C. G.; Laughlin, L. J.; Colmanet, S.; Scrofani, S. D. B. Inorg. Chem. 1996, 35, 5368.
297. Bristow, S.; Collison, D.; Garner, C. D.; Clegg, W. J. Chem. Soc., Dalton Trans. 1983, 2495.
298. Eagle, A. A.; Tiekink, E. R. T.; George, G. N.; Young, C. G. Inorg. Chem. 2001, 40, 4563.
299. Eagle, A. A.; Tiekink, E. R. T.; Young, C. G. J. Chem. Soc., Chem. Commun. 1991, 1746.
300. Faller, J. W.; Kucharczyk, R. R.; Ma, Y. Inorg. Chem. 1990, 29, 1662.
301. Barnard, K. R.; Gable, R. W.; Wedd, A. G. J. Biol. Inorg. Chem. 1997, 2, 623.
302. Eagle, A. A.; Gable, R. W.; Thomas, S.; Sproules, S. A.; Young, C. G. Polyhedron 2004, 23, 385.
303. Dean, F. M.; Goodchild, J.; Hill, A. W. J. Chem. Soc. C 1969, 2192.
304. (a) Jerumanis, S.; Lalancette, J. M. Can. J. Chem. 1964, 42, 1928.
305. (b) Greene, F. T.; Margrave, J. L. J. Am. Chem. Soc. 1959, 81, 5555.
306. Lebedev, E. P.; Baburina, V. A.; Reikhsfel'd, V. O. Zh. Obshch. Khim. 1974, 44, 1212.
307. (a) Money, J. K.; Huffman, J. C.; Christou, G. Inorg. Chem. 1985, 24, 3297.
308. (b) Money, J. K.; Folting, K.; Huffman, J. C.; Collison, D.; Temperley, J.; Mabbs, F. E.; Christou, G. Inorg. Chem. 1986, 25, 4583.
309. Do, Y.; Simhon, E. D.; Holm, R. H. Inorg. Chem. 1983, 22, 3809.
310. Do, Y.; Holm, R. H. Inorg. Chim. Acta 1985, 104, 33.
311. Drew, M. G. B.; Rice, D. A.; Williams, D. M. Inorg. Chim. Acta 1986, 118, 165.
312. Klemperer, W. G.; Schwartz, C. Inorg. Chem. 1985, 24, 4459.
313. Radkov, E.; Lu, Y.-J.; Beer, R. H. Inorg. Chem. 1996, 35, 551.
314. Tanner, L. D.; Haltiwanger, R. C.; Rakowski DuBois, M. Inorg. Chem. 1988, 27, 1741.
315. Minelli, M.; Enemark, J. H.; Wieghardt, K.; Hahn, M. Inorg. Chem. 1983, 22, 3952.
316. Do, Y.; Simhon, E. D.; Holm, R. H. Inorg. Chem. 1985, 24, 1831.
317. Yu, S.-B.; Holm, R. H. Inorg. Chem. 1989, 28, 4385.
318. Feinstein-Jaffe, I.; Dewan, J. C.; Schrock, R. R. Organometallics 1985, 4, 1189.
319. Partyka, D. V.; Holm, R. H. Inorg. Chem. 2004, 43, 8609.
320. Dorfman, J. R.; Girerd, J.-J.; Simhon, E. D.; Stack, T. D. P.; Holm, R. H. Inorg. Chem. 1984, 23, 4407.
321. Mukherjee, R. N.; Stack, T. D. P.; Holm, R. H. J. Am. Chem. Soc. 1988, 110, 1850.
322. Tacke, R.; Wannagat, U. Top. Curr. Chem. 1979, 84, 1.
323. Personal communication, Dr. William Steele, Oak Ridge National Laboratory and the University of Tennessee, Knoxville.
324. (a) So, J.-H.; Boudjouk, P. Synthesis 1989, 306.
325. (b) So, J.-H.; Boudjouk, P.; Hong, H. H.; Weber, W. P. Inorg. Synth. 1992, 29, 30.
326. (a) Housmekerides, C. E.; Pilato, R. S.; Geoffroy, G. L.; Rheingold, A. L. J. Chem. Soc., Chem. Commun. 1991, 563.
327. (b) Housmekerides, C. E.; Ramage, D. L.; Kretz, C. M.; Shontz, J. T.; Pilato, R. S.; Geoffroy, G. L.; Rheingold, A. L.; Haggerty, B. S. Inorg. Chem. 1992, 31, 4453.
328. (a) Newman, M. S.; Karnes, H. A. J. Org. Chem. 1966, 31, 3980.
329. (b) Kwart, H.; Evans, E. R. J. Org. Chem. 1966, 31, 410.
330. (c) Kurth, H.-J.; Kraatz, U.; Korte, F. Chem. Ber. 1973, 106, 2419.
331. (d) Kurth, H.-J.; Kraatz, U.; Korte, F. Liebigs Ann. Chem. 1976, 1313.
332. (e) Besserer, K.; Köhler, H.; Rundel, W. Chem. Ber. 1982, 115, 3678.
333. (f) Corral, C.; Lissavetzky, J.; Valdeolmillos, A. M. Synthesis 1984, 172.
334. (g) Aslam, M.; Davenport, K. G. Synth. Commun. 1987, 17, 1761.
335. (h) Beaulieu, F.; Snieckus, V. Synthesis 1992, 112.
336. (i) Gibbs, C. G.; Gutsche, C. D. J. Am. Chem. Soc. 1993, 115, 5389.
337. (j) Fabbri, D.; Delogu, G.; De Lucchi, O. J. Org. Chem. 1993, 58, 1748.
338. (k) Cossu, S.; De Lucchi, O.; Fabbri, D.; Valle, G.; Painter, G. F.; Smith, R. A. J. Tetrahedron 1997, 53, 6073.
339. (l) Rao, P.; Hosseini, M. W.; De Cian, A.; Fischer, J. Chem. Commun. 1999, 2169.
340. The Newman-Kwart rearrangement has also been referred to as the Newman-Karnes reaction in the literature.
341. See, for instance: Goddard, C. A. Polyhedron 1997, 16, 4273.
342. Chatt, J.; Dilworth, J. R. J. Chem. Soc., Chem. Commun. 1974, 508.
343. Bishop, M. W.; Chatt, J.; Dilworth, J. R. J. Chem. Soc., Dalton Trans. 1979, 1.
344. Laplaza, C. E.; Davis, W. M.; Cummins, C. C. Angew. Chem., Int. Ed. Engl. 1995, 34, 2042.
345. Lorenz, I.-P.; Pohl, W.; Polborn, K. Chem. Ber. 1996, 129, 11.
346. Caskey, S. R.; Stewart, M. H,; Kivela, J. E.; Sootsman, J. R.; Johnson, M. J. A.; Kampf, J. W. J. Am. Chem. Soc. 2005, 127, 16750.
347. Khan, M. M. T.; Siddiqui, M. R. H. Inorg. Chem. 1991, 30, 1157.
348. Kendall, J. D.; Simpkins, N. S. Synlett 1998, 391.
349. For further examples of organic transformations catalyzed by dirhodium paddlewheel compounds, see: (a) Doyle, M. P.; Phillips, I. M. Tetrahedron Lett. 2001, 42, 3155.
350. (b) Doyle, M. P.; Phillips, I. M.; Hu, W. J. Am. Chem. Soc. 2001, 123, 5366.
351. (c) Lee, D.; Otte, R. D. J. Org. Chem. 2004, 69, 3569.
352. (d) Fruit, C.; Müller, P. Tetrahedron: Asymmetry 2004, 15, 1019.
353. (e) Lou, Y.; Horikawa, M.; Kloster, R. A.; Hawryluk, N. A.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 8916.
354. (f) Shi, W.; Zhang, B.; Zhang, J.; Liu, B.; Zhang, S.; Wang, J. Org. Lett. 2005, 7, 3103.
355. (g) Doyle, M. P.; Morgan, J. P.; Fettinger, J. C.; Zavalij, P. Y.; Colyer, J. T.; Timmons, D. J.; Carducci, M. D. J. Org. Chem. 2005, 70, 5291.
356. Jacob, J.; Espenson, J. H. Chem. Commun. 1999, 11, 1003.