Conclusions
Initiation of the reaction for the cyclization of isoprenoids by acids proceeds as a nonstereospecific process at the 2,3 bond, while when this reaction is initiated by mercury salts it proceeds as a stereospecific reaction.
Literature cited
A. V. Semenovsky, W. A. Smit, V. F. Kucherov, and I. G. Mursakulov, Tetrahedron,23, 1621 (1967).
M. T. Mustafaeva, V. A. Smit, V. A. Kuzovkin, and V. F. Kucherov, Izv. Akad. Nauk SSSR, Ser. Khim., 384 (1972).
M. Kurbanov, A. V. Semenovskii, and V. A. Smit, Izv. Akad. Nauk SSSR, Ser. Khim., 390 (1972); V. A. Smit, A. V. Semenovskii, and V. F. Kucherov, Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 312 (1962); V. A. Smit, A. V. Semenovskii, and F. F. Kucherov, Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 2193 (1960).
M. Kurbanov, A. V. Semenovskii, V. A. Smit, and V. F. Kucherov, Izv. Akad. Nauk SSSR, Ser. Khim., 2541 (1971).
M. Kurbanov, A. V. Semenovsky, W. A. Smit, L. V. Shmelev, and V. F. Kucherov, Tetrahedron Letters, 2175 (1972).
N. S. Zefirov, Usp. Khim.,34, 1272 (1965).
W. Wechfer, G. Slomp, F. McKellar, R. Wiechert, and N. Kerb, Tetrahedron,21, 1625 (1965).
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1151–1153, May, 1973.
Rights and permissions
About this article
Cite this article
Mustafaeva, M.T., Smit, V.A., Semenovskii, A.V. et al. Stereochemistry of protonation and mercuration of trisubstituted double bond during cyclization of isoprenoids. Russ Chem Bull 22, 1111–1113 (1973). https://doi.org/10.1007/BF00854264
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00854264