"Ortho-Effect" in thermal curtius rearrangement of alkylbenzoyl azides into isocyanates: A quantitative interpretation

Russian Chemical Bulletin

Volumn 56, Issue 1, 2007, Pages 7-13

  Zabalov, M V ^a   Tiger, R P ^b  

^a MOSCOW STATE UNIVERSITY   (Russian Federation)

^b SEMENOV INSTITUTE OF CHEMICAL PHYSICS   (Russian Federation)

Author keywords

"Ortho effect"; Acyl azides; Quantum chemical calculations; Reaction mechanism; Thermal Curtius rearrangement

Indexed keywords

EID: 34249890795     PISSN: 10665285     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11172-007-0002-7     Document Type: Article

References (18)

1. R. P. Tiger, Vysokomolek. Soedin., Ser. B, 2004, 46, 931
2. [Polym. Sci., Ser. B, 2004, 46, 142 (Engl. Transl.)].
3. W. Lwowsky, Nitrenes, Interscience, New York, 1970.
4. T. F. Goryainova, Yu. A. Ershov, and R. M. Livshits, Khim. Vys. Energ., 1975, 9, 99
5. [High Energy Chem. 1975, 9 (Engl. Transl.)].
6. E. A. Pritchina, N. P. Gritsan, A. Maltsev, T. Bally, T. Autrey, Y. Liu, Y. Wang, and J. P. Toscano, Phys. Chem. Chem. Phys., 2003, 5, 1010.
7. J. Liu, S. Mandel, C. M. Hadad, and M. S. Platz, J. Org. Chem., 2004, 69, 8583.
8. M. V. Zabalov and R. P. Tiger, Izv. Akad Nauk. Ser. Khim., 2005, 2200
9. [Russ. Chem. Bull., Int. Ed., 2005, 54, 2270].
10. M. R. Brinkman, D. Rethell, and Z. J. Hayes, Tetrahedron Lett., 1973, 989.
11. M. S. Newman, S. H. Lee, and A. B. Garrett, J. Am. Chem. Soc., 1947, 69, 113.
12. Y. Yukawa and Y. Tsuno, J. Am. Chem. Soc., 1958, 80, 6346.
13. J. Muller, Kinetic und Mechanismus der Curtius Umlagerung, Dissertation, University München, München, 1962.
14. V. A. Pal'm, Osnovy kolichestvennoi teorii organicheskikh reaktsii [Foundations of Quantitative Theory of Organic Reactions], Khimiya, Leningrad, 1977 (in Russian).
15. J. P. Perdew, K. Burke, and M. Ernzerhoff, Phys. Rev. Lett., 1996, 77, 3865.
16. M. Ernzerhoff and G. E. Scuseria, J. Chem. Phys., 1999, 110, 5029.
17. D. N. Laikov, Chem. Phys. Lett., 1997, 281, 151.
18. D. J. am Ende, K. M. De Vries, P. J. Clifford, and S. Brenek, J. Org. Proc Res. Dev., 1998, 2, 382.