"Carbon dichloride": Dihalocarbenes sixty years after hine (1, 2)

Journal of Organic Chemistry

Volumn 75, Issue 17, 2010, Pages 5773-5783

  Moss, Robert A ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION PARAMETER; AROMATIC ETHER; LASER FLASH PHOTOLYSIS;

OLEFINS; PHOTOLYSIS;

ETHERS;

ALKENE DERIVATIVE; AMIDINE; AROMATIC COMPOUND; AZIRINE DERIVATIVE; CARBENOID; CARBON; CARBON DICHLORIDE; CHLORIDE; DIHALOCARBENE DERIVATIVE; ETHER DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; COMPLEX FORMATION; ELECTROPHILICITY; KINETICS; LASER; NUCLEOPHILICITY; OXIDATION; PHOTOLYSIS; PRECURSOR; REVIEW; SOLVATION; SYNTHESIS;

EID: 77956158799     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100390p     Document Type: Review

References (95)

1. Presented in part at the Arthur C. Cope Award Symposium at the 240th American Chemical Society National Meeting in Boston, MA, August 24, 2010.
2. This perspective article incorporates some material previously reviewed in: Moss, R. A. J. Phys. Org. Chem. 2010, 23, 293
3. Hine, J. J. Am. Chem. Soc. 1950, 72, 2438
4. 2. The carbene nomenclature was originated by W. v. E. Doering, S. Winstein, and R. B. Woodward "in a nocturnal Chicago taxi and later delivered diurnally" at the 1951 Boston ACS meeting; cf. Doering, W.v.E.; Knox, L. H. J. Am. Chem. Soc. 1956, 78, 4947, ref 9.
5. Geuther, A. Ann. 1862, 123, 121
6. Nef, J. U. Ann. 1897, 298, 367
7. Thiele, J.; Dent, F. Ann. 1898, 302, 273
8. Mossler, G. Monatsheft 1903, 29, 573
9. Hine, J. Divalent Carbon; Ronald Press: New York, 1964; p 36f.
10. Hine, J.; Dowell, A. M., Jr. J. Am. Chem. Soc. 1954, 76, 2688
11. Hine, J.; Burske, N. W.; Hine, M.; Langford, P. B. J. Am. Chem. Soc. 1957, 79, 1406
12. Hine, J.; Ehrenson, S. J. J. Am. Chem. Soc. 1958, 80, 824
13. Hine, J.; Prosser, F. P. J. Am. Chem. Soc. 1958, 80, 4282
14. Hine, J.; Langford, P. B. J. Am. Chem. Soc. 1957, 79, 5497
15. Hine, J.; Ketley, A. D. J. Org. Chem. 1960, 25, 606
16. Doering, W.v.E.; Hoffmann, A. K. J. Am. Chem. Soc. 1954, 76, 6162
17. For a recent review, see: Fedorynski, M. Chem. Rev. 2003, 103, 1099.
18. Dehmlow, E. V. In Carbene (Carbenoide) Methoden der Organischen Chemie (Houben-Weyl); Regitz, M., Ed.; Thieme Verlag: Stuttgart, 1989; Vol. E19b, pp 1521 - 1589.
19. Makosza, M.; Wawrzyniewicz Tetrahedron Lett. 1969, 10, 4659
20. Makosza, M. Pure Appl. Chem. 1975, 43, 439
21. Wagner, W. M. Proc. Chem. Soc. 1959, 229
22. Wagner, W. M.; Kloosterziel, H.; Van der Ven, S. Rec. Trav. Chim. Pays-Bas 1961, 80, 740
23. Parham, W. E.; Schweizer, E. E. J. Org. Chem. 1959, 24, 1733
24. Seyferth, D. Acc. Chem. Res. 1972, 5, 65
25. Seyferth, D.; Burlitch, J. M.; Minasz, R. J.; Mui, J.Y.-P.; Simmons, H. D., Jr.; Treiber, A. J. H.; Dowd, S. R. J. Am. Chem. Soc. 1965, 87, 4259
26. Köbrich, G.; Büttner, H.; Wagner, E. Angew. Chem., Int. Ed. Engl. 1970, 9, 169
27. Jones, M., Jr.; Sachs, W. H.; Kulczycki, A.; Waller, F. J. J. Am. Chem. Soc. 1966, 88, 3167
28. Hartwig, J. F.; Jones, M., Jr.; Moss, R. A.; Lawrynowicz, W. Tetrahedron Lett. 1986, 27, 5907
29. Chateuneuf, J. E.; Johnson, R. P.; Kirchoff, M. M. J. Am. Chem. Soc. 1990, 112, 3217
30. Presolski, S. I.; Zorba, A.; Thamattor, D. M.; Tippmann, E. M.; Platz, M. S. Tetrahedron Lett. 2004, 45, 485
31. Graham, W. H. J. Am. Chem. Soc. 1965, 87, 4396
32. Moss, R. A. Acc. Chem. Res. 2006, 39, 267
33. See ref 26 for essential references and a detailed discussion.
34. Wlostowska, J.; Moss, R. A.; Guo, W.; Chang, M. J. Chem. Commun. 1982, 432
35. Chu, G.; Moss, R. A.; Sauers, R. R. J. Am. Chem. Soc. 2005, 127, 14206
36. Moss, R. A.; Tian, J.; Sauers, R. R.; Ess, D. H.; Houk, K. N.; Krogh-Jespesen, K. J. Am. Chem. Soc. 2007, 129, 5167
37. Fedé, J.-M.; Jockusch, S.; Lin, N.; Moss, R. A.; Turro, N. J. Org. Lett. 2003, 5, 5027
38. Moss, R. A.; Perez, L. A.; Wlostowska, J.; Guo, W.; Krogh-Jespersen, K. J. Org. Chem. 1982, 47, 4177
39. In our intial preparation of dichlorodiazirine, (29) we used p -nitrophenoxychlorodiazirine instead of the 2,4-dinitrophenoxy derivative 9. The latter, however, proved to be a more reactive and better substrate. (30)
40. Moss, R. A.; Chu, G.; Sauers, R. R. J. Am. Chem. Soc. 2005, 127, 2408
41. Korkin, A. A.; Schleyer, P.v.R.; Boyd, R. J. Chem. Phys. Lett. 1994, 227, 312
42. Shaffer, C. J.; Esselman, B. J.; McMahon, R. J.; Stanton, J. F.; Woods, R. C. J. Org. Chem. 2010, 75, 1815
43. Moss, R. A.; Wang, L.; Krogh-Jespersen, K. J. Am. Chem. Soc. 2009, 131, 2128
44. Moss, R. A.; Tian, J.; Sauers, R. R.; Skalit, C.; Krogh-Jespersen, K. Org. Lett. 2007, 9, 4053
45. Cox, D. P.; Moss, R. A.; Terpinski, J. J. Am. Chem. Soc. 1983, 105, 6513
46. Moss, R. A.; Terpinski, J.; Cox, D. P.; Denney, D. Z.; Krogh-Jespersen, K. J. Am. Chem. Soc. 1985, 107, 2743
47. Mitsch, R. A. J. Heterocycl. Chem. 1966, 3, 245
48. Mitsch, R. A. J. Heterocycl. Chem. 1964, 1, 59
49. Mitsch, R. A. J. Org. Chem. 1968, 33, 1847
50. Zollinger, J. L.; Wright, C. D.; McBrady, J. J.; Dybvig, D. H.; Fleming, F. A.; Kurhajec, G. A.; Mitsch, R. A.; Neuvar, E. W. J. Org. Chem. 1973, 38, 1065
51. Meyers, M. D.; Frank, S. Inorg. Chem. 1966, 5, 1455
52. Mitsch, R. A.; Neuvar, E. W.; Koshar, R. J.; Dybvig, D. H. J. Heterocycl. Chem. 1965, 2, 371
53. Moss, R. A.; Zhang, M.; Krogh-Jespersen, K. Org. Lett. 2009, 11, 5702
54. Moss, R. A. Acc. Chem. Res. 1980, 13, 58
55. Moss, R. A.; Zhang, M.; Krogh-Jespersen, K. Org. Lett. 2009, 11, 1947
56. Moss, R. A.; Tian, J. J. Am. Chem. Soc. 2005, 127, 8960
57. Moss, R. A.; Tian, J. Org. Lett. 2006, 8, 1245
58. Moss, R. A.; Tian, J. Tetrahedron Lett. 2006, 47, 3419
59. -.
60. Doering, W.v.E.; Henderson, W. A., Jr. J. Am. Chem. Soc. 1958, 80, 5274
61. Skell, P. S.; Garner, A. Y. J. Am. Chem. Soc. 1956, 78, 5430
62. Moss, R. A. Acc. Chem. Res. 1989, 22, 15
63. Rondan, N. G.; Houk, K. N.; Moss, R. A. J. Am. Chem. Soc. 1980, 102, 1770
64. For a recent review, see: Moss, R. A. In Carbene Chemistry: From Fleeting Intermediates to Powerful Reagents; Bertrand, G., Ed.; Dekker: New York, 2002; p 57f.
65. Moss, R. A.; Wang, L.; Zhang, M.; Skalit, C.; Krogh-Jespersen, K. J. Am. Chem. Soc. 2008, 130, 5634
66. Moss, R. A.; Tian, J.; Sauers, R. R.; Krogh-Jespersen, K. J. Am. Chem. Soc. 2007, 129, 10019
67. Krogh-Jespersen, K.; Yan, S.; Moss, R. A. J. Am. Chem. Soc. 1999, 121, 6269
68. Moss, R. A.; Wang, L.; Odorisio, C. M.; Zhang, M.; Krogh-Jespersen, K. J. Phys. Chem. A 2010, 114, 209
69. 2 carbonyl oxide which absorbs at 465 nm. (30)
70. The origin of this barrier is discussed below.
71. Moss, R. A.; Wang, L.; Odorisio, C. M.; Krogh-Jespersen, K. Tetrahedron Lett. 2010, 51, 1467
72. The C(3) π-complex should absorb at 511 nm (f ∼ 0.1) and most likely correlates with the observed absorbance at 532 nm. A computed O -ylidic complex, absorbing at 464 nm, is not observed. (59)
73. Turro, N. J.; Lehr, G. F.; Butcher, J. A., Jr.; Moss, R. A.; Guo, W. J. Am. Chem. Soc. 1982, 104, 1754
74. Houk, K. N.; Rondan, N. G. J. Am. Chem. Soc. 1984, 106, 4293
75. Houk, K. N.; Rondan, N. G.; Mareda, J. Tetrahedron 1985, 41, 1555
76. Jackson, J. E.; Soundararajan, N.; Platz, M. S.; Liu, M. T. H. J. Am. Chem. Soc. 1988, 110, 5595
77. Tippmann, E. M.; Platz, M. S.; Svir, I. B.; Klymenko, O. J. Am. Chem. Soc. 2004, 126, 5750
78. Moss, R. A.; Wang, L.; Weintraub, E.; Krogh-Jespersen, K. J. Phys. Chem. A 2008, 112, 4651
79. For a review, see: Moss, R. A. In Carbenes; Jones, M., Jr.; Moss, R. A., Eds.; Wiley: New York, 1973; p 153 f.
80. For phenylchlorocarbene additions, see: Turro, N. J.; Butcher, J. A.; Moss, R. A.; Guo, W.; Munjal, R. C.; Fedorynski, M. J. Am. Chem. Soc. 1980, 102, 7576
81. Robert, M.; Snoonian, J. R.; Platz, M. S.; Wu, G.; Hong, H.; Thamattoor, D. M.; Jones, M., Jr. J. Phys. Chem. A 1988, 102, 587
82. Ehrenson, R. T. C.; Brownlee, R. W.; Taft, R. W. Prog. Phys. Org. Chem. 1973, 10, 1
83. Moss, R. A.; Zhang, M. Org. Lett. 2008, 10, 4045
84. Moss, R. A.; Lawrynowicz, W.; Turro, N. J.; Gould, I. R.; Cha, Y. J. Am. Chem. Soc. 1986, 108, 7028
85. Gould, I. R.; Turro, N. J.; Butcher, J. A., Jr.; Doublday, C. E., Jr.; Hacker, N. P.; Lehr, G. F.; Moss, R. A.; Cox, D. P.; Guo, W.; Munjal, R. C.; Perez, L. A.; Fedorynski, M. Tetrahedron 1985, 41, 1587
86. Skell, P. S.; Cholod, M. S. J. Am. Chem. Soc. 1969, 91, 7131
87. Giese, B.; Meister, J. Angew. Chem., Int. Ed. Engl. 1978, 17, 595
88. Giese, B.; Lee, W.-B. Angew. Chem., Int. Ed. Engl. 1980, 19, 835
89. Giese, B.; Lee, W.-B.; Meister, J. Ann. Chem. 1980, 725
90. Giese, B.; Lee, W.-B. Chem. Ber. 1981, 114, 3306
91. Blake, J. F.; Wierschke, S. G.; Jorgensen, W. L. J. Am. Chem. Soc. 1989, 111, 1919
92. See the summary in ref 53.
93. 2 (26.5). (51)
94. 2/TME addition. (44)
95. 2, 1.89; MeOCCl, 2.46. (51)