Issue 12, 1991

Alkynylhalocarbenes: generation from 1,1-dihaloalk-2-ynes by base solvolysis and reaction with alkenes

Abstract

A series of 1,1-dihaloalk-2-ynes 1–3 has been prepared by halogenation of the formylacetylenes 8 with PCl5 or an equimolar mixture of PCl5 and Br2. A simple, general means of access to the alkynylhalocarbenes 5 has been developed via base-initiated α-elimination of 1,1-dihaloalk-2-ynes (13). The carbenes 5ai have been trapped by alkenes, to form 1-alkynyl-1-halocyclopropanes (11) in up to 90% yield. Under the same conditions compound 1g was converted into the buta-diene 12. Experimental evidence for the electrophilicity and the singlet nature of carbenes 5 has been obtained.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1991, 1875-1881

Alkynylhalocarbenes: generation from 1,1-dihaloalk-2-ynes by base solvolysis and reaction with alkenes

K. N. Shavrin, I. V. Krylova, I. B. Shvedova, G. P. Okonnishnikova, I. E. Dolgy and O. M. Nefedov, J. Chem. Soc., Perkin Trans. 2, 1991, 1875 DOI: 10.1039/P29910001875

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