Compounds of the menthane series. Synthesis of unsaturated primary alcohols with the o- and p-menthane skeletons


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Abstract

Precursors to terpene alcohols of the o- and p-menthane series (o-cimen-7-ol and o- and p-cimen-9-ols) were synthesized, and their reduction with lithium in ethylenediamine was studied. The reduction of o- and p-cimen-9-ols in the presence of isopropyl alcohol selectively afforded the corresponding 1,4-dihydro derivatives. Under analogous conditions, o-cimen-7-ol was converted into a mixture of unsaturated hydrocarbons. The reduction with lithium in ethylenediamine in the absence of isopropyl alcohol in all cases gave mixtures of menthene alcohols.

About the authors

P. I. Fedorov

I.N. Ul’yanov Chuvash State University

Author for correspondence.
Email: paf@myrambler.ru
Russian Federation, Moskovskii pr. 15, Cheboksary, 428015

T. P. Fedorova

I.N. Ul’yanov Chuvash State University

Email: paf@myrambler.ru
Russian Federation, Moskovskii pr. 15, Cheboksary, 428015

V. P. Sheverdov

I.N. Ul’yanov Chuvash State University

Email: paf@myrambler.ru
Russian Federation, Moskovskii pr. 15, Cheboksary, 428015

G. P. Pavlov

I.N. Ul’yanov Chuvash State University

Email: paf@myrambler.ru
Russian Federation, Moskovskii pr. 15, Cheboksary, 428015

A. V. Eremkin

I.N. Ul’yanov Chuvash State University

Email: paf@myrambler.ru
Russian Federation, Moskovskii pr. 15, Cheboksary, 428015

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