Stable noncyclic singlet carbenes

Chemical Reviews

Volumn 109, Issue 8, 2009, Pages 3333-3384

  Vignolle, Joan ^a,b,c,d   Cattoën, Xavier ^a,b,c,e   Bourissou, Didier ^a  

^a UNIVERSITÉ DE TOULOUSE   (France)

^b CNRS   (France)

^c UNIVERSITY OF CALIFORNIA   (United States)

^d UNIVERSITY OF CALIFORNIA   (United States)

^e INSTITUT CHARLES GERHARDT   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BOND ANGLE; CARBENES; GEOMETRIC CONSTRAINT;

AMINES; ELECTRONIC STRUCTURE; TRANSITION METALS;

COORDINATION REACTIONS;

EID: 68949147041     PISSN: 00092665     EISSN: 15206890     Source Type: Journal    
DOI: 10.1021/cr800549j     Document Type: Review

References (317)

1. (a) Doering, W. v. E.; Hoffmann, A. K. J. Am. Chem. Soc. 1954, 76, 6162.
2. (b) Fischer, E. O.; Maasböl, A. Angew. Chem., Int. Ed. Engl. 1964, 3, 580.
3. Igau, A.; Grützmacher, H.; Baceiredo, A.; Bertrand, G. J. Am. Chem. Soc. 1988, 110, 6463.
4. Arduengo, A. J., III; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361.
5. Major achievements have also been reported in the stabilization and characterization of triplet carbenes, see: (a) Tomioka, H. Acc. Chem. Res. 1997, 30, 315.
6. (b) Kirmse, W. Angew. Chem., Int. Ed. 2004, 43, 1767.
7. (c) Kawano, M.; Hirai, K.; Tomioka, H.; Ohashi, Y. J. Am. Chem. Soc. 2007, 129, 2383.
8. (a) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290.
9. (b) César, V.; Bellemin-Laponnaz, S.; Gade, L. H. Chem. Soc. Rev. 2004, 33, 619.
10. (c) Nair, V.; Santhamma, B.; Vellalath, S. Angew. Chem., Int. Ed. 2004, 43, 5130.
11. (d) Garrison, J. C.; Youngs, W. J. Chem. Rev. 2005, 105, 3978.
12. (e) Nolan, S. P. N-Heterocyclic Carbenes in Synthesis; Wiley-VCH: Weinheim, Germany, 2006.
13. (f) Tekavec, T. N.; Louie, J. Top. Organomet. Chem. 2007, 21, 195.
14. (g) Coord. Chem. Rev. 2007, 251 (5-6).
15. (a) Enders, D.; Niemeier, O.; Henseler, A. Chem. Rev. 2007, 107, 5606.
16. (b) Enders, D.; Balensiefer, T. Acc. Chem. Res. 2004, 37, 534.
17. (c) Zeitler, K. Angew. Chem., Int. Ed. 2005, 44, 7506.
18. (d) Enders, D.; Balensiefer, T.; Niemeier, O.; Christmann, M. In Enantioselective Organocatalysis-Reactions and Experimental Procedures; Dalko, P. I., Ed.; Wiley-VCH: Weinheim, Germany, 2007; p 331.
19. (e) Marion, N.; Díez-González, S.; Nolan, S. P. Angew. Chem., Int. Ed. 2007, 46, 2988.
20. 3, see: (a) Frey, G. D.; Lavallo, V.; Donnadieu, B.; Schoeller, W. W.; Bertrand, G. Science 2007, 316, 439. For the reaction with CO, see:
21. (b) Lavallo, V.; Canac, Y.; Donnadieu, B.; Schoeller, W. W.; Bertrand, G. Angew. Chem., Int. Ed. 2006, 45, 3488. For the reaction with P4, see:
22. (c) Masuda, J.; Schoeller, W. W.; Donnadieu, B.; Bertrand, G. Angew. Chem., Int. Ed. 2007, 46, 7052.
23. For a recent account, see: Canac, Y.; Soleilhavoup, M.; Conejero, S.; Bertrand, G. J. Organomet. Chem. 2004, 689, 3857.
24. Bourissou, D.; Guerret, O.; Gabbaï, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39.
25. Bouhadir, G.; Bourissou, D. Chem. Soc. Rev. 2004, 33, 210.
26. For a detailed comparison between phosphorus and nitrogen in cation stabilization, see: (a) Kapp, J.; Schade, C.; El-Nahasa, A. M.; Schleyer, P. v. R. Angew. Chem., Int. Ed. Engl. 1996, 35, 2236.
27. Baceiredo, A.; Bertrand, G.; Sicard, G. J. Am. Chem. Soc. 1985, 107, 4781.
28. Gillette, G.; Baceiredo, A.; Bertrand, G. Angew. Chem., Int. Ed. Engl. 1990, 29, 1429.
29. 3 (R' =) Me, Ph, or c-Hex) are only transient species: (a) Soleilhavoup, M.; Alcaraz, G.; Réau, R.; Baceiredo, A.; Bertrand, G. Phosphorus, Sulfur, Silicon 1993, 76, 49.
30. (b) Emig, N.; Réau, R.; Bertrand, G. Tetrahedron Lett. 1995, 36, 4231.
31. Alcaraz, G.; Reed, R.; Baceiredo, A.; Bertrand, G. J. Chem. Soc., Chem. Commun. 1993, 1354.
32. Krysiak, J.; Lyon, C.; Baceiredo, A.; Gornitzka, H.; Mikolajczyk, M.; Bertrand, G. Chem.-Eur. J. 2004, 10, 1982.
33. Kato, T.; Gornitzka, H.; Baceiredo, A.; Savin, A.; Bertrand, G. J. Am. Chem. Soc. 2000, 122, 998.
34. (a) Nguyen, M. T.; McGinn, M. A.; Hegarty, A. F. Inorg. Chem. 1986, 25, 2185.
35. (b) Hoffmann, M. R.; Kuhler, K. J. Chem. Phys. 1991, 94, 8029.
36. (a) Nuylászi, L.; Szieberth, D.; Reffy, J.; Veszpremi, T. J. Mol. Struct. (THEOCHEM) 1998, 453, 91.
37. (b) Lecea, B.; Ayerbe, M.; Arrieta, A.; Cossío, F. P.; Branchadell, V.; Ortuño, R. M.; Baceiredo, A. J. Org. Chem. 2007, 72, 357.
38. Soleilhavoup, M.; Baceiredo, A.; Treutler, O.; Ahlrichs, R.; Nieger, M.; Bertrand, G. J. Am. Chem. Soc. 1992, 114, 10959.
39. Treutler, O.; Ahlrichs, R.; Soleilhavoup, M. J. Am. Chem. Soc. 1993, 115, 8788.
40. Bourissou, D.; Bertrand, G. C. R. Acad. Sci., Ser. B Paris 1996, 322, 489.
41. Dyer, P.; Baceiredo, A.; Bertrand, G. Inorg. Chem. 1996, 35, 46.
42. Alder, R. W.; Allen, P. R.; Murray, M.; Orpen, A. G. Angew. Chem., Int. Ed. Engl. 1996, 35, 1121.
43. Herrmann, W. A.; Ofele, K.; von Preysing, D.; Herdtweck, E. J. Organomet. Chem. 2003, 684, 235.
44. Alder, R. W.; Blake, M. E. Chem. Commun. 1997, 1513.
45. Frey, G. D.; Rentzsch, C. F.; von Preysing, D.; Scherg, T.; Mühlhofer, M.; Herdtweck, E.; Herrmann, W. A. J. Organomet. Chem. 2006, 691, 5725.
46. Herrmann, W. A.; Schutz, J.; Frey, G. D.; Herdtweck, E. Organometallics 2006, 25, 2437.
47. Frey, G. D.; Herrmann, W. A. J. Organomet. Chem. 2005, 690, 5876.
48. Alder, R. W.; Blake, M. E.; Bortolotti, C.; Bufali, S.; Butts, C. P.; Linehan, E.; Oliva, J. M.; Orpen, A. G.; Quayle, M. J. Chem. Commun. 1999, 241.
49. Alder, R. W.; Chaker, L.; Paolini, F. P. V. Chem. Commun. 2004, 2172.
50. Otto, M.; Conejero, S.; Canac, Y.; Romanenko, V. D.; Rudzevitch, V.; Bertrand, G. J. Am. Chem. Soc. 2004, 126, 1016.
51. Alder, R. W.; Blake, M. E.; Chaker, L.; Harvey, J. N.; Paolini, F.; Schütz, J. Angew. Chem., Int. Ed. 2004, 43, 5896.
52. Conejero, S.; Canac, Y.; Tham, F. S.; Bertrand, G. Angew. Chem., Int. Ed. 2004, 43, 4089.
53. Rosen, E. L.; Sanderson, M. D.; Saravanakumar, S.; Bielawski, C. W. Organometallics 2007, 26, 5774.
54. (a) Alcarazo, M.; Roseblade, S. J.; Alonso, E.; Fernández, R.; Alvarez, E.; Lahoz, F. L.; Lassaletta, J. M. J. Am. Chem. Soc. 2004, 126, 13242. For complexes deriving from N- dialkylamino-N'-alkylimidazolin-2-ylidenes and 4-dialkylamino-triazol-5- ylidenes, see also:
55. (b) Ros, A.; Monge, D.; Alcarazo, M.; Alvarez, E.; Lassaletta, J. M.; Fernández, R. Organometallics 2006, 25, 6039.
56. (c) Ros, A.; Alcarazo, M.; Iglesias-Siguenza, J.; Díez, E.; Alvarez, E.; Fernández, R.; Lassaletta, J. M. Organometallics 2008, 27, 4555.
57. Cattoën, X.; Miqueu, K.; Gornitzka, H.; Bourissou, D.; Bertrand, G. J. Am. Chem. Soc. 2005, 127, 3292.
58. Cattoën, X.; Gornitzka, H.; Tham, F. S.; Miqueu, K.; Bourissou, D.; Bertrand, G. Eur. J. Org. Chem. 2007, 912.
59. A similar value was also found in a diaminocarbene constrained geometrically by a [3]-ferrocenophane framework [119.2 (7)?]. (a) Khramov, D.; Rosen, E. L.; Lynch, E. L.; Bielawski, C. W. Angew. Chem., Int. Ed 2008, 47, 2267.
60. (b) Siemeling, U.; Färber, C.; Bruhn, C. Chem. Commun. 2009, 98.
61. (a) Heinemann, C.; Thiel, W. Chem. Phys. Lett. 1994, 217, 11.
62. (b) Alder, R. W.; Blake, M. E.; Oliva, J. M. J. Phys. Chem. A 1999, 103, 11200.
63. Cattoën, X. Thèse de l'Université Paul Sabatier, Toulouse, France, 2004.
64. Arduengo, A. J., III; Goerlich, J. R.; Marshall, W. J. Liebigs Ann. 1997, 365.
65. 3-1,3,4-oxadiazolines, see: (a) Couture, P.; Terlouw, J. K.; Warkentin, J. J. Am. Chem. Soc. 1996, 118, 4214.
66. (b) Warkentin, J. Acc. Chem. Res. 2009, 42, 205.
67. For a borane adduct and a palladium complex, see respectively: (a) Lambert, C.; Lopez-Solera, I.; Raithby, P. R. Organometallics 1996, 15, 452.
68. (b) Hahn, F. E.; Lugger, T.; Beinhoff, M. Z. Naturforsch. 2004, 59b, 196.
69. Alder, R. W.; Butts, C. P.; Orpen, A. G. J. Am. Chem. Soc. 1998, 120, 11526.
70. Merceron-Saffon, N.; Baceiredo, A.; Gornitzka, H.; Bertrand, G. Science 2003, 301, 1223.
71. Buron, C.; Gornitzka, H.; Romanenko, V.; Bertrand, G. Science 2000, 288, 834.
72. Schoeller, W. W. Eur. J. Inorg. Chem. 2000, 369.
73. Despagnet-Ayoub, E.; Gornitzka, H.; Bourissou, D.; Bertrand, G. Eur. J. Org. Chem. 2003, 2039.
74. Despagnet, E.; Gornitzka, H.; Rozhenko, A. B.; Schoeller, W. W.; Bourissou, D.; Bertrand, G. Angew. Chem., Int. Ed. 2002, 41, 2835.
75. Despagnet-Ayoub, E.; Solé, S.; Gornitzka, H.; Rozhenko, A.; Scholler, W. W.; Bourissou, D.; Bertrand, G. J. Am. Chem. Soc. 2003, 125, 124.
76. Solé, S.; Gornitzka, H.; Schoeller, W. W.; Bourissou, D.; Bertrand, G. Science 2001, 292, 1901.
77. Cattoën, X.; Gornitzka, H.; Bourissou, D.; Bertrand, G. J. Am. Chem. Soc. 2004, 126, 1342.
78. Vignolle, J.; Gornitzka, H.; Donnadieu, B.; Bourissou, D.; Bertrand, G. Angew. Chem., Int. Ed. 2008, 47, 2271.
79. MOP is a generic term for 2-phosphanyl-1,1'-binaphthyl, and MeOMOP stands for 2-phosphanyl-2'-methoxy-1,1'-binaphthyl.
80. Vignolle, J.; Asay, M.; Miqueu, K.; Bourissou, D.; Bertrand, G. Org. Lett. 2008, 10, 4299.
81. Canac, Y.; Conejero, S.; Soleilhavoup, M.; Donnadieu, B.; Bertrand, G. J. Am. Chem. Soc. 2006, 128, 459.
82. Lavallo, V.; Mafhouz, J.; Canac, Y.; Donnadieu, B.; Schoeller, W. W.; Bertrand, G. J. Am. Chem. Soc. 2004, 126, 8670.
83. (a) Cattoën, X.; Bourissou, D.; Bertrand, G. Tetrahedron Lett. 2006, 47, 531.
84. (b) Gómez-Bujedo, S.; Alcarazo, M.; Pichon, C.; Alvarez, E.; Fernández, R.; Lassaletta, J. M. Chem. Commun. 2007, 1180.
85. (a) Lavallo, V.; Canac, Y.; Präsang, C.; Donnadieu, B.; Bertrand, G. Angew. Chem., Int. Ed. 2005, 44, 5705.
86. (b) Lavallo, V.; Frey, G. D.; Kousar, S.; Donnadieu, B.; Bertrand, G. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 13569.
87. (c) Lavallo, V.; Frey, G. D.; Donnadieu, B.; Soleilhavoup, M.; Bertrand, G. Angew. Chem., Int. Ed. 2008, 47, 5224.
88. Merceron, N.; Miqueu, K.; Baceiredo, A.; Bertrand, G. J. Am. Chem. Soc. 2002, 124, 6806.
89. Canac, Y.; Conejero, S.; Donnadieu, B.; Schoeller, W. W.; Bertrand, G. J. Am. Chem. Soc. 2005, 127, 7312.
90. Vignolle, J.; Donnadieu, B.; Bourissou, D.; Bertrand, G. Tetrahedron Lett. 2007, 48, 685.
91. Goumri, S.; Leriche, Y.; Gornitzka, H.; Baceiredo, A.; Bertrand, G. Eur. J. Inorg. Chem. 1998, 1539.
92. Conejero, S.; Song, M.; Martin, D.; Canac, Y.; Soleilhavoup, M.; Bertrand, G. Chem. Asian J. 2006, 1, 155.
93. Frey, G. D.; Song, M. Y.; Bourg, J. B.; Donnadieu, B.; Soleilhavoup, M.; Bertrand, G. Chem. Commun. 2008, 4711.
94. (a) Keller, H.; Maas, G.; Regitz, M. Tetrahedron Lett. 1986, 27, 1903.
95. (b) Svara, J.; Fluck, E.; Riffel, H. Z. Naturforsch. 1985, 40b, 1258.
96. (c) Neumüller, B.; Fluck, E. Phosphorus Sulfur 1987, 29, 23.
97. (a) Hoffmann, R.; Gleiter, R.; Mallory, F. B. J. Am. Chem. Soc. 1970, 92, 1460.
98. (b) Carter, E. A.; Goddard, W. A., III J. Phys. Chem. 1986, 90, 998.
99. (c) Trinquier, G.; Malrieu, J. P. J. Am. Chem. Soc. 1987, 109, 5303.
100. (d) Malrieu, J. P.; Trinquier, G. J. Am. Chem. Soc. 1989, 111, 5916.
101. (e) Jacobsen, H.; Ziegler, T. J. Am. Chem. Soc. 1994, 116, 3667.
102. Chen, Y. T.; Jordan, F. J. Org. Chem. 1991, 56, 5029.
103. Weiss, R.; Huber, S. M.; Heinemann, F. W.; Audebert, P.; Pühlhofer, F. G. Angew. Chem., Int. Ed. 2006, 45, 8059.
104. Poliakov, D.; Rogalyov, A.; Shevchenko, I. Eur. J. Org. Chem. 2008, 5805.
105. Poliakov, D.; Rogalyov, A.; Shevchenko, I. Tetrahedron Lett. 2007, 48, 6798.
106. For a general review on organocatalysis with stable nucleophilic carbenes, see ref 6a.
107. (a) Halleux, A. Angew. Chem., Int. Ed. Engl. 1964, 3, 752.
108. (b) Boyer, J.; Beverung, W. J. Chem. Soc., Chem. Commun. 1969, 1377.
109. (c) Green, J. A.; Singer, L. A. Tetrahedron Lett. 1969, 5093.
110. (d) Obata, N.; Takizawa, T. Tetrahedron Lett. 1969, 3403.
111. (e) Ciganek, E. J. Org. Chem. 1970, 35, 862.
112. (a) Igau, A.; Baceiredo, A.; Trinquier, G.; Bertrand, G. Angew. Chem., Int. Ed. Engl. 1989, 28, 621.
113. (b) Gillette, G.; Igau, A.; Baceiredo, A.; Bertrand, G. New. J. Chem. 1991, 15, 393.
114. Lentz, D.; Anibarro, M.; Preugschat, D.; Bertrand, G. J. Fluor. Chem. 1998, 89, 73.
115. Amsallem, D.; Mazières, S.; Piquet-Fauré, V.; Gornitzka, H.; Baceiredo, A.; Bertrand, G. Chem.-Eur. J. 2002, 8, 5305.
116. Marrot, S.; Kato, T.; Cossío, F. P.; Gornitzka, H.; Baceiredo, A. Angew. Chem., Int. Ed. 2006, 45, 7447.
117. (a) Ammann, J. R.; Subramanian, R.; Sheridan, R. S. J. Am. Chem. Soc. 1992, 114, 7592.
118. (b) Visser, P.; Zuhse, R.; Wong, M. W.; Wentrup, C. J. Am. Chem. Soc. 1996, 118, 12598.
119. Lyashchuk, S. N.; Skrypnik, Y. G. Tetrahedron Lett. 1994, 35, 5271.
120. Dixon, D. A.; Arduengo, A. J.; Dobbs, K. D.; Khasnis, D. V. Tetrahedron Lett. 1995, 36, 645.
121. Winter, S.; Pracejus, H. Chem. Ber. 1966, 99, 151.
122. Romanenko, V. D.; Gudima, A. O.; Chernega, A. N.; Bertrand, G. Inorg. Chem. 1992, 31, 3493.
123. Romanenko, V.; Gudima, A. O.; Chernega, A. N.; Sotiropoulos, J.-M.; Alcaraz, G.; Bertrand, G. Bull. Soc. Chim. Fr. 1994, 131, 748.
124. (a) Niecke, E.; Gudat, D. Angew. Chem., Int. Ed. Engl. 1991, 30, 217.
125. (b) Schoeller, W. W. In Multiple Bonds and Low Coordination in Phosphorus Chemistry; Regitz, M., Scherer, O. J., Eds.; Thieme: Stuttgart, Germany, 1990; p 5.
126. (c) Schoeller, W. W.; Niecke, E. J. Chem. Soc., Chem. Commun. 1982, 569.
127. (d) Schoeller, W. W.; Busch, T.; Nieman, J.; Dabisch, T.; Stohrer, W. D. Heteroatom 1991, 2, 213.
128. (e) Niecke, E. In Multiple Bonds and Low Coordination in Phosphorus Chemistry; Regitz, M., Scherer, O. J., Eds.; Thieme: Stuttgart, Germany, 1990; p 293.
129. (f) Niecke, E.; Gudat, D.; Schoeller, W. W.; Rademacher, P. J. Chem. Soc., Chem. Commun. 1985, 1050.
130. (a) Regitz, M.; Maas, G. Diazo Compounds. Properties and Synthesis; Academic Press: Orlando, FL, 1986; Chapter 2.
131. (b) Glaser, R.; Chen, G. S.; Barnes, C. L. J. Org. Chem. 1993, 58, 7446.
132. Hopkins, J. M.; Bowdridge, M.; Robertson, K. N.; Cameron, T. S.; Jenkins, H. A.; Clyburne, J. A. C. J. Org. Chem. 2001, 66, 5713.
133. Staudinger, H.; Meyer, J. Helv. Chim. Acta 1919, 2, 635.
134. (a) Moss, R. A. In Carbene Chemistry; Bertrand, G., Ed.; Marcel Dekker: New York, 2002.
135. (b) Jones, M., Jr.; Moss, R. A. In Reactive Intermediate Chemistry; Moss, R. A., Platz, M. S., Jones, M., Jr., Eds.; Wiley-interscience: Hoboken, NJ, 2004.
136. Goumri-Magnet, S.; Kato, T.; Gornitzka, H.; Baceiredo, A.; Bertrand, G. J. Am. Chem. Soc. 2000, 122, 4464.
137. Krysiak, J.; Kato, T.; Gornitzka, H.; Baceiredo, A.; Mikolajczyk, M.; Bertrand, G. J. Org. Chem. 2001, 66, 8240.
138. Solé, S.; Cattoën, X.; Gornitzka, H.; Bourissou, D.; Bertrand, G. Tetrahedron Lett. 2004, 45, 5391.
139. Ye, Q.; Komarov, I. V.; Kirby, A. J.; Jones, M., Jr. J. Org. Chem. 2002, 67, 9288.
140. (a) Illa, O.; Gornitzka, H.; Baceiredo, A.; Bertrand, D.; Branchadell, V.; Ortuño, R. M. J. Org. Chem. 2003, 68, 7707.
141. (b) Illa, O.; Gornitzka, H.; Branchadell, V.; Baceiredo, A.; Bertrand, D.; Ortuño, R. M. Eur. J. Org. Chem. 2003, 3147.
142. Illa, O.;Álvarez-Larena, Á.; Baceiredo, A.; Branchadell, V.; Ortũno, R. M. Tetrahedron: Asymmetry 2007, 18, 2617.
143. Transient electrophilic carbenes are known to react with nitriles to give transient or even stable nitrile ylides:(a) Padwa, A.; Hornbuckle, S. F. Chem. Rev. 1991, 91, 263.
144. (b) Janulis, E. P.; Wilson, S. R.; Arduengo, A. J., III Tetrahedron Lett. 1984, 25, 405.
145. (a) Alcaraz, G.; Wecker, U.; Baceiredo, A.; Dahan, F.; Bertrand, G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1246.
146. (b) Piquet, V.; Baceiredo, A.; Gornitzka, H.; Dahan, F.; Bertrand, G. Chem.-Eur. J. 1997, 3, 1757.
147. The reaction of tert-butylphosphaalkyne with the transient dichlorocarbene affords a P-chloro 1H-phosphirene via [1 + 2]-cycloaddition followed by C → P shift of a chlorine atom: (a) Wagner, O.; Ehle, M.; Regitz, M. Angew. Chem., Int. Ed. Engl. 1989, 28, 225.
148. (b) Memmesheimer, H.; Regitz, M. Rev. Heteroatom. Chem. 1994, 10, 61.
149. (a) Armbrust, R.; Sanchez, M.; Réau, R.; Bergsträsser, U.; Regitz, M.; Bertrand, G. J. Am. Chem. Soc. 1995, 117, 10785.
150. (b) Sanchez, M.; Réau, R.; Gornitzka, H.; Regitz, M.; Bertrand, G. J. Am. Chem. Soc. 1997, 119, 9720.
151. (c) Sanchez, M.; Réau, R.; Marsden, C. J.; Regitz, M.; Bertrand, G. Chem.-Eur. J. 1999, 5, 274.
152. Bertrand, G. Heteroatom. 1991, 2, 29.
153. See, for example:(a) Moss, R. A.; Ho, G. J. J. Am. Chem. Soc. 1990, 112, 5642.
154. (b) Kirmse, W. In Advances in Carbene Chemistry; Brinker, U. H., Ed.; Jai Press: Greenwich, CT, 1994; Vol. 1, pp 1-57.
155. Menu, M.-J.; Dartiguenave, Y.; Dartiguenave, M.; Baceiredo, A.; Bertrand, G. Phosphorus, Sulfur Silicon 1990, 47, 327.
156. (a) Arduengo, A. J.; Calabrese, J. C.; Davidson, F.; Dias, H. R. V.; Goerlich, J. R.; Krafczyk, R.; Marshall, W. J.; Tamm, M.; Schmutzler, R. Helv. Chim. Acta 1999, 82, 2348.
157. (b) Lloyd-Jones, G. C.; Alder, R. W.; Owen-Smith, G. J. J. Chem.-Eur. J. 2006, 12, 5361.
158. (c) Korotkikh, N. I.; Rayenko, G. F.; Shvaika, O. P.; Pekhtereva, T. M.; Cowley, A. H.; Jones, J. N.; MacDonald, C. L. B. J. Org. Chem. 2003, 68, 5762.
159. Nyce, G.; Csihony, S.; Waymouth, R. M.; Hedrick, J. L. Chem.-Eur. J. 2004, 10, 4073-4079.
160. Casalnuovo, A. L.; Calabrese, J. C.; Milstein, D. Inorg. Chem. 1987, 26, 941.
161. 2 by a stable digermyne, see: (a) Spikes, G. H.; Fettinger, J. C.; Power, P. P. J. Am. Chem. Soc. 2005, 127, 12232. For the reversible activation and transfer of dihydrogen with frustrated phosphine boranes, see :
162. (b) Welch, G. C.; Juan, R. R. S.; Masuda, J. D.; Stephan, D. W. Science 2006, 314, 1124.
163. (c) Chase, P. A.; Welch, G. C.; Jurca, T.; Stephan, D. W. Angew. Chem., Int. Ed. 2007, 46, 8050.
164. (d) Stephan, D. W. Org. Biomol. Chem. 2008, 6, 1535.
165. (e) Spies, P.; Schwendemann, S.; Lange, S.; Kehr, G.; Frohlich, R.; Erker, G. Angew. Chem., Int. Ed. 2008, 47, 7543.
166. Appel, R.; Huppertz, M.; Westerhaus, A. Chem. Ber. 1983, 116, 114.
167. Baceiredo, A.; Igau, A.; Bertrand, G.; Menu, M.-J.; Dartiguenave, Y.; Bonnet, J.-J. J. Am. Chem. Soc. 1986, 108, 7868.
168. Igau, A.; Baceiredo, A.; Bertrand, G. New J. Chem. 1989, 13, 359.
169. Poliakov, D.; Shevchenko, I. Eur. J. Org. Chem. 2007, 2055.
170. (a) Culkin, D. A.; Jeong, W. H.; Csihony, S.; Gomez, E. D.; Balsara, N. R.; Hedrick, J. L.; Waymouth, R. M. Angew. Chem., Int. Ed. 2007, 46, 2627.
171. (b) Kamber, N. E.; Jeong, W.; Waymouth, R. M.; Pratt, R. C.; Lohmeijer, B. G. G.; Hedrick, J. L. Chem. Rev. 2007, 107, 5813.
172. Jeong, W.; Hedrick, J. L.; Waymouth, R. M. J. Am. Chem. Soc. 2007, 129, 8414.
173. (a) Nickon, A. Acc. Chem. Res. 1993, 26, 84.
174. (b) Sander, W.; Bucher, G.; Wierlacher, S. Chem. Rev. 1993, 93, 1583.
175. (c) Sulzbach, H. M.; Platz, M. S.; Schaeffer, H. F., III; Hadad, C. M. J. Am. Chem. Soc. 1997, 119, 5682.
176. (d) Merrer, D. C.; Moss, R. A. In Advances in Carbene Chemistry; Brinker, U., Brinker, H., Eds.;Elsevier: Am-sterdam, The Netherlands, 2001; Vol. 3.
177. (e) Bonneau, R. In Advances in Carbene Chemistry; Brinker, U. H., Ed.; JAI Press, Stamford, CT, 1998; Vol. 2.
178. The chlorotrifluoromethylcarbene was found to rearrange into chlorotrifluoroethylene upon irradiation at 10 K in a matrix: Seburg, R. A.; McMahon, R. J. J. Org. Chem. 1993, 58, 979.
179. N C 1,2-migration reactions have scarcely been reported with NHCs and cross-over experiments have supported intermolecular mechanism: (a) Solé, S.; Gornitzka, H.; Guerret, O.; Bertrand, G. J. Am. Chem. Soc. 1998, 120, 9100.
180. (b) Poyatos, M.; McNamara, W.; Incarvito, C.; Clot, E.; Peris, E.; Crabtree, R. H. Organometallics 2008, 27, 2128.
181. Cattoën, X.; Solé, S.; Pradel, C.; Gornitzka, H.; Miqueu, K.; Bourissou, D.; Bertrand, G. J. Org. Chem. 2003, 68, 911.
182. (a) Alder, R. W.; Allen, P. R.; Williams, S. J. J. Chem. Soc., Chem. Commun. 1995, 1267.
183. (b) Kim, Y.-J.; Streitwieser, A. J. Am. Chem. Soc. 2002, 124, 5757.
184. (c) Amyes, T. L.; Diver, S. T.; Richard, J. P.; Rivas, F. M.; Toth, K. J. Am. Chem. Soc. 2004, 126, 4366.
185. (a) Guerret, O.; Bertrand, G. Acc. Chem. Res. 1997, 30, 486.
186. (b) Grützmacher, H.; Marchand, C. M. Coord. Chem. Rev. 1997, 163, 287.
187. 2) were proposed to occur via protonation of the carbene center, followed by rapid coupling of the ensuing ion pair: (a) Martin, D.; Illa, O.; Baceiredo, A.; Bertrand, G.; Ortuño, R. M.; Branchadell, V. J. Org. Chem. 2005, 70, 5671.
188. Dixon, D. A.; Dobbs, K. B.; Arduengo, A. J., III; Bertrand, G. J. Am. Chem. Soc. 1991, 113, 8782.
189. Magill, A. M.; Cavell, K. J.; Yates, B. F. J. Am. Chem. Soc. 2004, 126, 8717.
190. Igau, A.; Grützmacher, H.; Pritzkow, H.; Baceiredo, A.; Bertrand, G. J. Am. Chem. Soc. 1989, 111, 6853.
191. Ehrig, M.; Horn, H.; Kolmel, C.; Ahlrichs, R. J. Am. Chem. Soc. 1991, 113, 3701.
192. Locquenghien, K. H. v.; Baceiredo, A.; Boese, R.; Bertrand, G. J. Am. Chem. Soc. 1991, 113, 5062.
193. Cowley, A.; Gabbaï, F. P.; Carrano, C. J.; Mokry, L. M.; Bond, M. R.; Bertrand, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 578.
194. Beste, A.; Kramer, O.; Gerhard, A.; Frenking, G. Eur. J. Inorg. Chem. 1999, 2037.
195. Arduengo, A. J., III; Davidson, F.; Krafczyk, R.; Marshall, W. J.; Schmutzler, R. Monatsh. Chem. 2000, 131, 251.
196. Kato, T.; Gornitzka, H.; Baceiredo, A.; Schoeller, W. W.; Bertrand, G. Science 2000, 289, 754.
197. (a) Kato, T.; Gornitzka, H.; Baceiredo, A.; Schoeller, W. W.; Bertrand, G. J. Am. Chem. Soc. 2002, 124, 2506.
198. (b) Martin, D.; Gornitzka, H.; Baceiredo, A.; Bertrand, G. Eur. J. Inorg. Chem. 2005, 2619.
199. The reaction of transient dihalogenocarbenes with phosphines is the most efficient preparative route to C-dihalogeno phosphorus ylides: (a) Bestmann, H. J.; Zimmermann, R. In Methoden der Organischen Chemie (Houben-Weyl); Regitz, M., Ed.; Georg Thieme Verlag: Stuttgart, Germany, 1982; Vol. E1, p 616.
200. (b) Johnson, A. W.; Kaska, W. C.; Starzewski, K. A. O.; Dixon, D. A. In Ylides and Imines of Phosphorus; Wiley: New York, 1993; p 115.
201. Oediger, H.; Möller, F.; Eiter, K. Synthesis 1972, 591.
202. (a) Reed, R.; Réau, R.; Dahan, F.; Bertrand, G. Angew. Chem., Int. Ed. Engl. 1993, 32, 399.
203. (b) Bouhadir, G.; Reed, R. W.; Réau, R.; Bertrand, G. Heteroatom Chem. 1995, 6, 371.
204. Dyer, P.; Guerret, O.; Dahan, F.; Baceiredo, A.; Bertrand, G. J. Chem. Soc., Chem. Commun. 1995, 2339.
205. Soleilhavoup, M.; Baceiredo, A.; Bertrand, G. Angew. Chem., Int. Ed. Engl. 1993, 32, 1167.
206. Goumri-Magnet, S.; Polishchuk, O.; Gornitzka, H.; Marsden, C. J.; Baceiredo, A.; Bertrand, G. Angew. Chem., Int. Ed. Engl. 1999, 38, 3727.
207. Goumri-Magnet, S.; Gornitzka, H.; Baceiredo, A.; Bertrand, G. Angew. Chem., Int. Ed. Engl. 1999, 38, 678.
208. + is the only other α-(metallomethylene) phosphorane isolated to date: Bestmann, H. J.; Schmidt, M. Angew. Chem., Int. Ed. Engl. 1987, 26, 79.
209. (a) Schlosser, M.; Kadibelban, T.; Steinhoff, G. Angew. Chem., Int. Ed. Engl. 1966, 5, 968.
210. (b) Corey, E. J.; Kang, J. J. Am. Chem. Soc. 1982, 104, 4724.
211. (c) Corey, E. J.; Kang, J.; Kyler, K. Tetrahedron Lett. 1985, 26, 555.
212. (a) Moss, R. A. Acc. Chem. Res. 1999, 32, 969. Homolytic β-fragmentation reactions have been investigated theoretically and evidenced experimentally for transient (di)alkoxycarbenes:
213. (b) Feller, D.; Borden, W. T.; Davidson, E. R. J. Comput. Chem. 1980, 1, 158.
214. (c) Venneri, P. C.; Warkentin, J. J. Am. Chem. Soc. 1998, 120, 11182.
215. (d) Reid, D. L.; Warkentin, J. J. Chem. Soc., Perkin Trans. 2 2000, 1980.
216. (e) Reid, D. L.; Hernandez-Trujillo, J.; Warkentin, J. J. Phys. Chem. A 2000, 104, 3398.
217. (f) Merkley, N.; El-Saidi, M.; Warkentin, J. Can. J. Chem. 2000, 78, 356.
218. (g) Merkley, N.; Warkentin, J. Can. J. Chem. 2000, 78, 942: Transient conjugated cyclopropylcarbenes have been shown to decompose via a radical pathway:
219. (h) Cummins, J. M.; Porter, T. A.; Jones, M., Jr. J. Am. Chem. Soc. 1998, 120, 6473.
220. Merceron-Saffon, N. Thèse de l'Université Paul Sabatier, Toulouse, France, 2003.
221. Despagnet, E.; Miqueu, K.; Gornitzka, H.; Dyer, P.; Bourissou, D.; Bertrand, G. J. Am. Chem. Soc. 2002, 124, 11834.
222. Denk, K.; Sirsch, P.; Herrmann, W. A. J. Organomet. Chem. 2002, 649, 219.
223. (a) Tafipolsky, M.; Scherer, W.; Ofele, K.; Artus, G.; Pedersen, B.; Herrmann, W. A.; McGrady, G. S. J. Am. Chem. Soc. 2002, 124, 5865.
224. (b) Frey, G. D.; Herdtweck, E.; Herrmann, W. A. J. Organomet. Chem. 2006, 691, 2465.
225. Lee, M.-T.; Hu, C.-H. Organometallics 2004, 23, 976.
226. Pd-arene and Pd-X (X) O, N) interactions have been shown both experimentally and theoretically to play a crucial role in the unique behavior of biaryl phosphines in Pd-catalyzed cross-coupling reactions:(a) Walker, S. D.; Barder, T. E.; Martinelli, J. R.; Buchwald, S. L. Angew. Chem., Int. Ed. 2004, 43, 1871.
227. (b) Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685.
228. (c) Billingsley, K. L.; Barder, T. E.; Buchwald, S. L. Angew. Chem., Int. Ed. 2007, 46, 5359.
229. (d) Barder, T. E.; Biscoe, M. R.; Buchwald, S. L. Organometallics 2007, 26, 2183.
230. (a) Kočovský, P.; Vyskočil, S.; Císař ová, I.; Sejbal, J.; Tišlerová, I.; Smrčina, M.; Lloyd-Jones, G. C.; Stephen, S. C.; Butts, C. P.; Murray, M.; Langer, V. J. Am. Chem. Soc. 1999, 121, 7714.
231. (b) Lloyd-Jones, G. C.; Stephen, S. C.; Murray, M.; Butts, C. P.; Vyskočil, S.; Kočovský, P. Chem.-Eur. J. 2000, 6, 4348.
232. (c) Kočovský, P.; Vyskočil, S.; Smrčina, M. Chem. Rev. 2003, 103, 3213.
233. (d) Dotta, P.; Kumar, P. G. A.; Pregosin, P. S.; Albinati, A.; Rizzato, S. Organometallics 2003, 22, 5345.
234. (e) Kumar, P. G. A.; Dotta, P.; Hermatschweiler, R.; Pregosin, P. S.; Albinati, A.; Rizzato, S. Organometallics 2005, 24, 1306.
235. (a) Merceron-Saffon, N.; Gornitzka, H.; Baceiredo, A.; Bertrand, G. J. Organomet. Chem. 2004, 689, 1431.
236. (b) Teuma, E.; Lyon-Saunier, C.; Gornitzka, H.; Mignani, G.; Baceiredo, A.; Bertrand, G. J. Organomet. Chem. 2005, 690, 5541.
237. Vignolle, J.; Donnadieu, B.; Bourissou, D.; Soleilhavoup, M.; Bertrand, G. J. Am. Chem. Soc. 2006, 128, 14810.
238. Schwindt, M. A.; Miller, J. R.; Hegedus, L. S. J. Organomet. Chem. 1991, 413, 143, and references therein.
239. Licandro, E.; Maiorana, S.; Papagani, A.; Perdicchia, D.; Manzotti, R. Chem. Commun. 1999, 925.
240. (a) Imwinkelried, R.; Hegedus, L. S. Organometallics 1988, 7, 702.
241. (b) Schwindt, M. A.; Lejon, T.; Hegedus, L. S. Organometallics 1990, 9, 2814.
242. Meca, L.; Dvořák, D.; Ludvík, J.; Císařová, I.; Š těpnicka, P. Organometallics 2004, 23, 2541.
243. (a) Licandro, E.; Maiorana, S.; Manzotti, R.; Papagani, A.; Perdicchia, D.; Pryce, M.; Tiripicchio, A.; Lanfranchi, M. Chem. Commun. 1998, 383.
244. (b) Licandro, E.; Maiorana, S.; Perdicchia, D.; Baldoli, C.; Graiff, C.; Tiripicchio, A. J. Organomet. Chem. 2001, 617-618, 399.
245. Hartshorn, A. J.; Lappert, M. F.; Turner, K. J. Chem. Soc., Dalton Trans. 1978, 348.
246. (a) Cetinkaya, B; Lappert, M. F.; Turner, K. J. Chem. Soc., Chem. Commun. 1972, 851.
247. (b) Cetinkaya, B; Lappert, M. F.; McLaughlin, G. M.; Turner, K. J. Chem. Soc., Dalton Trans. 1974, 1591.
248. Kremzow, D.; Seidel, G.; Lehmann, C. W.; Fürstner, A. Chem.-Eur. J. 2005, 11, 1833.
249. Michelin, R. A.; Pombeiro, A. J. L.; Guedes da Silva, M. F. C. Coord. Chem. Rev. 2001, 218, 75.
250. Badley, E. M.; Chatt, J.; Richards, R. L.; Sim, G. A. J. Chem. Soc. D 1969, 1322.
251. (b) Canovese, L.; Visentin, F.; Uguagliati, P.; Crociani, B.; Di Bianca, F. J. Organomet. Chem. 1997, 535, 69.
252. (a) Crociani, B.; Boschi, T.; Belluco, U. Inorg. Chem. 1970, 9, 2021.
253. (b) Albeniz, A. C.; Espinet, P.; Manrique, R.; Perez-Mateo, A. Chem.-Eur. J. 2005, 11, 1565.
254. Angelici, R. J.; Charley, L. M. J. Organomet. Chem. 1970, 24, 205.
255. Acyclic aminocarbene gold(I) complexes, prepared from coordinated isocyanides, display interesting mesomorphic and luminescence properties: (a) Zhang, S. W.; Ishii, R.; Takahashi, S. Organometallics 1997, 16, 20.
256. (b) White-Morris, R. L.; Olmstead, M. M.; Jiang, F.; Tinti, D. S.; Balch, A. L. J. Am. Chem. Soc. 2002, 124, 2327.
257. (c) White-Morris, R. L.; Olmstead, M. M.; Jiang, F.; Balch, A. L. Inorg. Chem. 2002, 41, 2313.
258. Aumann, R.; Jasper, B.; Fröhlich, R. Organometallics 1996, 15, 1942.
259. (a) Chugaev, L.; Skarana-Grigorieva, M. J. Russ. Chem. Soc. 1915, 47, 776.
260. (b) Chugaev, L.; Skarana-Grigorieva, M.; Posniak, A. Z. Anorg. Allg. Chem. 1925, 148, 37.
261. (c) Burke, A.; Balch, A. L.; Enemark, J. H. J. Am. Chem. Soc. 1970, 92, 2555.
262. (d) Moncada, A. I.; Khan, M. A.; Slaughter, L. G. M. Tetrahedron Lett. 2005, 46, 1399.
263. (e) Moncada, A. I.; Tanski, J. M.; Slaughter, L. G. M. J. Organomet. Chem. 2005, 690, 6247.
264. (f) Moncada, A. I.; Manne, S.; Tanski, J. M.; Slaughter, L. M. Organometallics 2006, 25, 491.
265. (g) Wanniarachchi, Y. A.; Slaughter, L. M. Organometallics 2008, 27, 1055.
266. (a) Wanniarachchi, Y. A.; Slaughter, L. M. Chem. Commun. 2007, 3294.
267. (b) Wanniarachchi, Y. A.; Kogiso, Y; Slaughter, L. M. Organometallics 2008, 27, 21.
268. Hou, H.; Gantzel, P. K.; Kubiak, C. P. Organometallics 2003, 22, 2817.
269. Hou, H.; Gantzel, P. K.; Kubiak, C. P. J. Am. Chem. Soc. 2003, 125, 9564.
270. Coalter, J. N.; Bollinger, J. C.; Huffman, J. C.; Werner-Zwanziger, U.; Caulton, K. G.; Davidson, E. R.; Gerard, H.; Clot, E.; Eisenstein, O. New J. Chem. 2000, 24, 9.
271. Standfest-Hauser, C. M.; Mereiter, K.; Schmid, R.; Kirchner, K. Organometallics 2002, 21, 4891.
272. (a) Kee, T. P.; Gibson, V. C.; Clegg, W. J. Organomet. Chem. 1987, 325, C14.
273. (b) Gibson, V. C.; Grebenik, P. D.; Green, M. L. H. J. Chem. Soc., Chem. Commun. 1983, 1101.
274. (c) Gibson, V. C.; Graimann, C. E.; Hare, P. M.; Green, M. L. H.; Bandy, J. A.; Grebenik, P. D.; Prout, K. J. Chem. Soc., Dalton Trans. 1985, 2025.
275. (d) Green, M. L. H.; Hare, P. M.; Bandy, J. A. J. Organomet. Chem. 1987, 330, 61.
276. (e) Hovnanian, N.; Hubert-Pfalzgraf, L. G.; Le Borgne, G. Inorg. Chem. 1985, 24, 4647.
277. Slugovc, C.; Mereiter, K.; Trofimenko, S.; Carmona, E. Angew. Chem., Int. Ed. 2000, 39, 2158.
278. Lee, D. H.; Chen, J. Y.; Faller, J. W.; Crabtree, R. H. Chem. Commun. 2001, 213.
279. Kuznetsov, V. F.; Lough, A. J.; Gusev, D. G. Chem. Commun. 2002, 2432.
280. Carrión, M. C.; García-Vaquero, E.; Jalón, F. A.; Manzano, B. R.; Weissensteiner, W.; Mereiter, K. Organometallics 2006, 25, 2298.
281. Rankin, M. A.; McDonald, R.; Ferguson, M. J.; Stradiotto, M. Organometallics 2005, 24, 4981.
282. Whited, M. T.; Grubbs, R. H. Organometallics 2008, 27, 5737.
283. (a) Romero, P. E.; Whited, M. T.; Grubbs, R. H. Organometallics 2008, 27, 3422.
284. (b) Whited, M. T.; Grubbs, R. H. J. Am. Chem. Soc. 2008, 130, 5874.
285. (c) Van der Boom, M. E. Angew. Chem., Int. Ed. 2009, 48, 28.
286. Whited, M. T.; Grubbs, R. H. J. Am. Chem. Soc. 2008, 130, 16476.
287. Liu, S. T.; Reddy, K. R. Chem. Soc. Rev. 1999, 28, 315.
288. Albéniz, A.; Espinet, P.; Manrique, R.; Pérez-Mateo, A. Angew. Chem., Int. Ed. 2002, 41, 2469.
289. Crudden, C. M.; Allen, D. P. Coord. Chem. Rev. 2004, 248, 2247, and references therein.
290. (a) Vyboishchikov, S. F.; Frenking, G. Chem.-Eur. J. 1998, 4, 1428.
291. (b) Frenking, G.; Sola, M.; Vyboishchikov, S. F. J. Organomet. Chem. 2005, 690, 6178.
292. Lai, C.-L.; Guo, W.-H.; Lee, M.-T.; Hu, C.-H. J. Organomet. Chem. 2005, 690, 5867.
293. Schoeller, W. W.; Eisner, D.; Grigoleit, S.; Rozhenko, A. J. B.; Alijah, A. J. Am. Chem. Soc. 2000, 122, 10115.
294. Schoeller, W. W.; Rozhenko, A. J. B.; Alijah, A. J. Organomet. Chem. 2001, 617, 435.
295. Bourissou, D.; Bertrand, G. Adv. Organomet. Chem. 1999, 44, 175.
296. Miqueu, K.; Despagnet-Ayoub, E.; Dyer, P. W.; Bourissou, D.; Bertrand, G. Chem.-Eur. J. 2003, 9, 5858.
297. Such a peculiar bonding situation has been evidenced within a few NHC complexes of high-valent metal chlorides: (a) Abernethy, C. D.; Codd, G. M.; Spicer, M. D.; Taylor, M. K. J. Am. Chem. Soc. 2003, 125, 1128.
298. (b) Braband, H.; Abram, U. Chem. Commun. 2003, 2436.
299. (c) Shukla, P.; Johnson, J. A.; Vidovic, D.; Cowley, A. H.; Abernethy, C. D. Chem. Commun. 2004, 360.
300. (a) Fröhlich, N.; Pidun, U.; Stahl, M.; Frenking, G. Organometallics 1997, 16, 442.
301. (b) Maron, L.; Bourissou, D. Organometallics 2007, 26, 1100.
302. Dhudshia, B.; Thadani, A. N. Chem. Commun. 2006, 668.
303. For recent applications of hydrogen-bonded diaminocarbene gold(I) complexes to the skeletal rearrangement and methoxycyclization of 1,6-enynes, see: Bartolome, C.; Ramiro, Z.; Pérez-Galán, P.; Bour, C.; Raducan, M.; Echavarren, A. M.; Espinet, P. Inorg. Chem. 2008, 47, 11391.
304. (a) Nakafuji, S. Y.; Kobayashi, J.; Kawashima, T. Angew. Chem., Int. Ed. 2008, 47, 1141.
305. (b) Kobayashi, J.; Nakafuji, S.-Y.; Yatabe, A.; Kawashima, T. Chem. Commun. 2008, 6233.
306. (c) Asay, M.; Donnadieu, B.; Baceiredo, A.; Soleilhavoup, M.; Bertrand, G. Inorg. Chem. 2008, 47, 3949.
307. (d) Fürstner, A.; Alcarazo, M.; Radkowski, K.; Lehmann, C. Angew. Chem., Int. Ed. 2008, 47, 8302.
308. (a) Saalfrank, R. W.; Maid, H. Chem. Commun. 2005, 5953.
309. (b) Hahn, F. E. Angew. Chem., Int. Ed. 2008, 47, 4057.
310. For related developments in push-push allenes, including carbodicarbenes, see: (a) Tonner, R.; Frenking, G. Angew. Chem., Int. Ed. 2007, 46, 8695.
311. (b) Tonner, R.; Frenking, G. Chem.-Eur. J. 2008, 14, 3260.
312. (c) Tonner, R.; Frenking, G. Chem.-Eur. J. 2008, 14, 3273.
313. (d) Dyker, C. A.; Lavallo, V.; Donnadieu, B.; Bertrand, G. Angew. Chem., Int. Ed. 2008, 47, 3206.
314. (e) Fürstner, A.; Alcarazo, M.; Goddard, R.; Lehmann, C. W. Angew. Chem., Int. Ed. 2008, 47, 3210.
315. The interconversion between the singlet and triplet states of 2-naphthyl(carbomethoxy)carbene has been spectroscopically evidenced: (a) Zhu, Z.; Bally, T.; Stracener, L. L.; McMahon, R. J. J. Am. Chem. Soc. 1999, 121, 2863.
316. (b) Wang, Y.; Yuzawa, T.; Hamaguchi, H.; Toscano, J. P. J. Am. Chem. Soc. 1999, 121, 2875.
317. (c) Wang, J. L.; Likhotvorik, I.; Platz, M. S. J. Am. Chem. Soc. 1999, 121, 2883.