Reactivity of 1-chloro-3-phenyldiazirines

Journal of Organic Chemistry

Volumn 71, Issue 13, 2006, Pages 5012-5015

  Martinu, Tomas ^a   Dailey, William P ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1-CHLORO-3-PHENYLDIAZIRINES; BROMIDE IONS; ELECTRON DONOR; P-SUBSTITUTED 1-CHLORO-3-PHENYLDIAZIRINES (5),;

BROMINE COMPOUNDS; ELECTRONS; NEGATIVE IONS; PROBABILITY DENSITY FUNCTION; REACTION KINETICS; SUBSTITUTION REACTIONS;

AROMATIC HYDROCARBONS;

1 CHLORO 3 PHENYLDIAZIRINE DERIVATIVE; 3 BROMO 3 PHENYLDIAZIRINE; 3 CHLORO 3 PHENYLDIAZIRINE; AZIRINE DERIVATIVE; BENZAMIDINE DERIVATIVE; BROMIDE; CHLORINE; FUNCTIONAL GROUP; N,N,N' TRICHLOROBENZAMIDINE; UNCLASSIFIED DRUG;

[1,3] SIGMATROPIC SHIFT; ARTICLE; BINDING AFFINITY; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHEMOREACTIVITY; DENSITY FUNCTIONAL THEORY; ELECTRON; EXPERIMENT; REACTION ANALYSIS; STOICHIOMETRY; SUBSTITUTION REACTION; TRANSITION STRUCTURE;

DIAZOMETHANE; MODELS, CHEMICAL; MOLECULAR STRUCTURE;

EID: 33745454559     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060341g     Document Type: Article

References (30)

1. Graham, W. H. J. Am. Chem. Soc. 1965, 87, 4396.
2. (a) Wlostowska, J.; Moss, R. A.; Guo, W.; Chang, M. J. J. Chem. Soc., Chem. Commun. 1982, 432.
3. (b) Cox, D. P.; Moss, R. A.; Terpinski, J. J. Am. Chem. Soc. 1983, 105, 6513.
4. (c) Creary, X. Acc. Chem. Res. 1992, 25, 31.
5. (d) Moss, R. A. Acc. Chem. Res. 2006, 39, 267.
6. (a) Pittman, C. U., Jr.; Kress, A.; Patterson, T. B.; Wallon, P.; Kispert, L. D. J. Org. Chem. 1974, 39, 373.
7. (b) Byun, Y.-G.; Saebo, S.; Pittman, C. U. J. Am. Chem. Soc. 1991, 113, 3689.
8. Krogh-Jespersen, K. Tetrahedron Lett. 1980, 21, 4553.
9. Moss, R. A.; Terpinski, J.; Cox, D. P.; Denney, D. Z.; Krogh-Jespersen, K. J. Am. Chem. Soc. 1985, 107, 2743.
10. Moss, R. A.; Fedorynski, M.; Kmiedk-Lawrynowicz, G.; Terpinski, J. Tetrahedron Lett. 1986, 27, 2707.
11. Moss, R. A.; Wlostowska, J.; Guo, W.; Fedorynski, M.; Springer, J. P.; Hirshfield, J. M. J. Org. Chem. 1981, 46, 5048.
12. (a) Creary, X.; Sky, A. F. J. Org. Chem. 1988, 53, 4637.
13. (b) Moss, R. A.; Fede, J. M.; Yan, S. J. Am. Chem. Soc. 2000, 122, 9878.
14. Dailey, W. P. Tetrahedron Lett. 1987, 28, 5801.
15. Bainbridge, K. E.; Dailey, W. P. Tetrahedron Lett. 1989, 30, 4901.
16. Creary, X.; Sky, A. F. J. Am. Chem. Soc. 1990, 112, 368.
17. (a) Padwa, A.; Eastman, D. J. Org. Chem. 1969, 34, 2728.
18. (b) Moss, R. A.; Cox, D. P.; Tomioka, H. Tetrahedron Lett. 1984, 25, 1023.
19. Alcaraz, G.; Baceiredo, A.; Nieger, M.; Bertrand, G. J. Am. Chem. Soc. 1994, 116, 2159.
20. (a) Creary, X.; Sky, A. F.; Phillips, G. J. Org. Chem. 1990, 55, 2005.
21. (b) Creary, X. J. Org. Chem. 1993, 58, 7700.
22. (a) Creary, X.; Sky, A. F.; Phillips, G.; Alonso, D. E. J. Am. Chem. Soc. 1993, 115, 7584.
23. (b) Moss, R. A.; Xue, S.; Liu, W. J. Am. Chem. Soc. 1994, 116, 10821.
24. Krogh-Jespersen, K.; Young, C. M.; Moss, R. A.; Wlostowski, M. Tetrahedron Lett. 1982, 23, 2339.
25. Martinu, T.; Dailey, W. P. J. Org. Chem. 2004, 69, 7359.
26. Pischel, H.; Holy, A.; Wagner, G. Collect. Czech. Chem. Commun. 1981, 46, 933.
27. Terpinski, J.; Denney, D. Z.; Beveridge, R.; Cox, D. P.; Moss, R. A. Magn. Reson. Chem. 1987, 25, 923.
28. 3-stabilized diazirinyl anion to form 4a. The anion would result from a single-electron transfer (SET) to 5a. followed by the loss of chloride ion and another SET.
29. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Kiene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision B.05; Gaussian, Inc.: Pittsburgh, PA, 2003.
30. Kim, C. K.; Li, H. G.; Lee, B.-S.; Kim, C. K.; Lee, H. W.; Lee, I. J. Org. Chem. 2002, 67, 1953.