Issue 6, 1988

Regioreversed nucleophilic substitution of 2-(allyloxy)benzothiazole by allylic Grignard reagents. A regioselective synthesis of 1,5-dienes

Abstract

2-(Allyloxy)benzothiazoles react with allylic organomagnesium compounds in the presence of copper bromide to give 1,5-dienes. The C–C coupling occurs almost exclusively in a head-to-tail fashion. Contrary to this the same electrophiles, when complexed with copper(I) bromide before the addition of the allylic Grignard reagents, give only 1,5-dienes derived from a head-to-head coupling process. The change in the selectivity is probably due to the co-ordinative effects of the substrates towards the organometallic species.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1988, 1301-1304

Regioreversed nucleophilic substitution of 2-(allyloxy)benzothiazole by allylic Grignard reagents. A regioselective synthesis of 1,5-dienes

V. Calo, L. Lopez and G. Pesce, J. Chem. Soc., Perkin Trans. 1, 1988, 1301 DOI: 10.1039/P19880001301

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