Kinetics of the reaction of phenylchlorocarbene with an azabicyclobutane

Tetrahedron Letters

Volumn 37, Issue 33, 1996, Pages 5849-5852

  Moss, Robert A ^a   Maksimovic, Ljiljana ^a   Marchand, Alan P ^b   Ramanaiah, K C V ^b  

^a RUTGERS UNIVERSITY   (United States)

^b UNIVERSITY OF NORTH TEXAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO COMPOUND; CHLORINATED HYDROCARBON; CYCLOBUTANE DERIVATIVE; PENTANE; PHENYLCHLOROCARBENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CHROMATOGRAPHY; CONTROLLED STUDY; EXCIMER LASER; PHOTOLYSIS; REACTION ANALYSIS;

EID: 0030581393     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01245-2     Document Type: Article

References (21)

1. (1) Excellent literature surveys and fundamental studies of these reactions appear in (a) Jackson, J.E.; Mock, G.B.; Tetef, M.L.; Zheng, G-x; Jones, M., Jr. Tetrahedron 1985, 41, 1453.
2. (b) Xu, L.; Miebach, T.; Brinker, U.H. Tetrahedron Lett. 1991, 32, 4461.
3. (2) Doering, W.v.E.; Coburn, J.F., Jr. Tetrahedron Lett. 1965, 991.
4. (3) Grigorev, A.E.; Tarakanova, A.V.; Milvitskaya, E.M.; Pisanov, N.V.; Morozova, N.M.; Platé, A.F. Moscow Univ. Chem. Bull. (Engl.) 1980, 32, 97 [cited in ref. 1b].
5. 1b it is a side bond that cleaves. In both cases, the former carbene carbon assumes negative charge, while positive charge resides on the appropriate substrate carbon.
6. (5) Scaiano, J. C.; McGarry, P.F. Tetrahedron Lett. 1993, 34, 1243.
7. 3.
8. (7) Kirmse, W. Carbene Chemistry, 2nd Ed., Academic Press, New York, 1971, pp. 409ff.
9. (8) Padwa, A.; Hornbuckle, S.F. Chem. Rev. 1991, 91, 263.
10. (9) (a) Bonneau, R.; Liu, M.T.H. J. Am. Chem. Soc. 1991, 113, 9872.
11. (b) Bonneau, R.; Reuter, I.; Liu, M.T.H. J. Am. Chem. Soc. 1994, 116, 3145.
12. (c) Liu, M.T.H. Romashin,; Y.N.; Venkatachalam, T.K. Can J. Chem. 1994, 72, 1961.
13. (10) For previous studies of reactions of 3 with various electrophiles, see Marchand, A.P.; Rajagopal, D.; Bott, S.G.; Archibald, T.G. J. Org. Chem. 1995, 60, 4943, and references cited therein. The preparation of 3 is described in Marchand, A.P.; Rajagopal, D.; Bott, S.G.; Archibald, T.G. J. Org. Chem. 1994, 59, 1608.
14. (10) For previous studies of reactions of 3 with various electrophiles, see Marchand, A.P.; Rajagopal, D.; Bott, S.G.; Archibald, T.G. J. Org. Chem. 1995, 60, 4943, and references cited therein. The preparation of 3 is described in Marchand, A.P.; Rajagopal, D.; Bott, S.G.; Archibald, T.G. J. Org. Chem. 1994, 59, 1608.
15. (11) Graham, W.H. J. Am. Chem. Soc. 1965, 87, 4396.
16. (12) For other examples of this hydrolytic process, see Moss, R.A.; Jang, E.G.; Krogh-Jespersen, K. Tetrahedron Lett. 1995, 36, 1409.
17. (13) (a) Jackson, J.E.; Soundararajan, N.; Platz, M.S.; Liu, M.T.H. J. Am. Chem. Soc. 1988, 110, 5595.
18. (b) Jackson, J.E.; Platz, M.S. in Advances in Carbene Chemistry, Vol. 1, Brinker, U.H., Ed., JAI Press, Greenwich, Conn., 1994, pp. 89ff.
19. -1, in good agreement with the pyridine ylide-determined rate constant.
20. 1a
21. 1a,b