Reaction of dichloro- and dibromocarbenes with 2-(vinyloxy)-1,3-butadiene
Organic Chemistry
Received:
- 25 Downloads
Conclusions
A disubstituted multiple bond has the greatest activity in the reaction of 2-(vinyloxy)-1,3-butadiene with dichloro- and dibromocarbenes. The vinyloxy group stabilizes the transition state less effectively than the alkyl or aryl substituent.
Keywords
Transition State Butadiene Great Activity Dichloro Multiple Bond
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.
Preview
Unable to display preview. Download preview PDF.
Literature cited
- 1.W. V. E. Doering and W. A. Henderson, J. Am. Chem. Soc.,80, 5274 (1958).Google Scholar
- 2.A. Ledwith and H. J. Woods, J. Chem. Soc., B, 973 (1967).Google Scholar
- 3.P. S. Skell and M. S. Cholod, J. Am. Chem. Soc.,91, 7131 (1969).Google Scholar
- 4.Yu. V. Savinykh, V. S. Aksenov, and T. A. Bogatyreva, Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, No. 6, 111 (1975).Google Scholar
- 5.Yu. V. Savinykh and V. S. Aksenov, Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, No. 1, 92 (1977).Google Scholar
- 6.B. A. Trofimov, A. S. Atavin, and A. V. Gusarov, Izv. Akad. Nauk SSSR, Ser. Khim., 1457 (1971); B. A. Trofimov, N. I. Shergina, A. S. Atavin, É. I. Kositsyna, A. V. Gusarov, and G. M. Gavrilova, Zh. Prikl. Spektrosk.,14, 282 (1971); B. A. Trofimov, N. I. Shergina, A. S. Atavin, É. I. Kositsyna, A. V. Gusarov, and G. M. Gavrilova, Izv. Akad. Nauk SSSR, Ser. Khim., 116 (1972).Google Scholar
- 7.B. A. Trofimov, I. S. Emel'yanov, M. Ya. Yasel'man, A. S. Atavin, B. V. Prokop'ev, A. V. Gusarov, G. N. Vanyukhin, and M. M. Ovchinnikova, Reakts. Sposobnost Org. Soedin.,6, 934 (1969); B. A. Trofimov and I. S. Emel'yanov, Reakts. Sposobnost Org. Soedin.,7, 564 (1970).Google Scholar
- 8.Yu. A. Zhdanov and V. I. Minkin, Correlation Analysis in Organic Chemistry [in Russian], Izd. Rostov. Univ. (1966), p. 312; V. A. Palm, Principles of the Quantitative Theory of Organic Reactions [in Russian], Khimiya, Leningrad (1967), p. 115.Google Scholar
- 9.B. Cadioli and B. Fortunato, Gazz. Chim. Ital.,104, 369 (1974); C. Hirose and R. F. Cure, J. Mol. Spectrosc.,38, 358 (1971); R. Kh. Zacheslavskaya, L. Ya. Rappoport, B. A. Trofimov, and G. N. Petrov, Reakts. Sposobn. Org. Soedin.,13, 416 (1976).Google Scholar
- 10.T. A. Kornilova, Proceedings of the First All-Union Conference on the Chemistry of Carbenes and Their Analogs [in Russian], Moscow (1973), p. 180.Google Scholar
- 11.R. R. Kostikov, A. P. Molchanov, and A. Ya. Bespalov, Zh. Org. Khim.,10, 10 (1974).Google Scholar
- 12.B. A. Trofimov, A. V. Amosova, N. K. Gusarova, O. A. Tarasova, and M. G. Voronkov, Zh. Org. Khim.,11, 2225 (1975).Google Scholar
- 13.R. R. Kostikov and A. P. Molchanov, Zh. Org. Khim.,11, 1767 (1975).Google Scholar
- 14.R. R. Kostikov, A. P. Molchanov, and I. A. D'yakonov, Zh. Org. Khim.,7, 2297 (1971).Google Scholar
- 15.E. Streitwieser, Molecular Orbital Theory for Organic Chemists, Wiley (1961).Google Scholar
Copyright information
© Plenum Publishing Corporation 1979