Conclusions
-
1.
Depending on the order of the treatment of the reaction mixture, the cyclization of geranylacetone upon treatment with (CF3CO2)2Hg leads either to {ie2130-1} or to the corresponding 2,5,5,8a-tetramethylperhydrochromane.
-
2.
The cyclization is completely stereospecific and involves the formation of an ambident oxonium intermediate.
-
3.
The ClHg derivatives of these chromenes were isolated, thus proving the participation of the CF3−CO2Hg+ electrophile and permitting establishment of the conformation of the cis-A/B-chromene.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature Cited
M. Kurbanov, A. V. Semenovskii (Semenovsky), V. A. Smit (W. A. Smit), L. V. Shmelev, and V. F. Kucherov, Tetrahedron Lett., 2175 (1972).
M. T. Mustafaeva, V. A. Smit, A. V. Semenovskii, and V. F. Kucherov, Izv. Akad. Nauk SSSR, Ser. Khim., 1151 (1973).
A. I. Dyadchenko, A. V. Semenovskii, and V. A. Smit, Izv. Akad. Nauk SSSR, Ser. Khim., 2276 (1976).
V. L. Mizyuk and A. V. Semenovskii, Izv. Akad. Nauk SSSR, Ser. Khim., 2074 (1976).
O. V. Lyubinskaya, V. A. Smit, A. V. Semenovskii and V. F. Kucherov, Dokl. Akad. Nauk SSSR,203, 829 (1972).
F. A. L. Anet and J. Krane, Tetrahedron Lett., 3255 (1974).
Additional information
N. D. Zelenskii Institute of Organic Chemistry Academy of Sciences of the USSR, Moscow. Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2281–2284, October, 1976.
Rights and permissions
About this article
Cite this article
Dyadchenko, A.I., Semenovskii, A.V. & Smit, V.A. The cyclization of isoprenoid compounds. Russ Chem Bull 25, 2127–2130 (1976). https://doi.org/10.1007/BF02659531
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02659531