Issue 7, 1977

Replacement reactions of 1,1-dichloro-2,5-diphenylcyclopropabenzene with organometallic reagents

Abstract

The replacement of the chloro-substituents of 1,1-dichloro-2,5-diphenylcyclopropabenzene (1) can be effected by various organometallic reagents. The products of reaction with Grignard and organolithium reagents and with lithium aluminium hydride have been characterised. Although the gem-diethyl derivative (8) is the only isolated product in which the ring system is retained, spectroscopic evidence is presented which supports the involvement of 1,1-disubstituted cyclopropabenzenes in all the reactions. With methylmagnesium iodide, the cyclopropabenzene (1) suffers the equivalent of Grignard reduction to afford the unanticipated fluorene (25).

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1977, 735-740

Replacement reactions of 1,1-dichloro-2,5-diphenylcyclopropabenzene with organometallic reagents

B. Halton, A. D. Woolhouse and P. J. Milsom, J. Chem. Soc., Perkin Trans. 1, 1977, 735 DOI: 10.1039/P19770000735

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