Bull. Russ. Acad. Sci. Div. Chem. Sci. (Engl. Transl.) p. 885 - 891 (1992)
Update date:2022-08-02
Topics:
Shavrin, K. N.
Krylova, I. V.
Dolgii, I. E.
Nefedov, O. M.
1,1-Dichloro-2-alkynes R1C<*>CCHCl2 (4a-g: R1=Me, n-Pr, c-Pr, t-Bu, Ad, Nor, Ph) were synthesized with yields of 50-75percent by chlorination with PCl5 of formylacetylenes (3a-g), prepared by oxidation of propargyl alcohols (1a-d) with CrO3*Py*HCl complex or acidolysis of propargyl acetals (2a-c) in the presence of catalytic quantities of pyridine; the corresponding alkynylchlorocarbenes, R1C<*>CCCl (5a-g) were generated from them with powdered KOH in a two-phase system or t-BuOK. The latter were trapped by olefins with formation of 1-chloro-1-alkynylcyclopropanes (6a-t) with yields of up to 90percent.Keywords: alkynylchlorocarbenes, 1,1-dichloro-2-alkynes, basic solvolysis, interphase catalysis, 1-chloro-1-alkynylcyclopropanes.
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