Journal of the Chemical Society. Perkin transactions I p. 1301 - 1304 (1988)
Update date:2022-08-05
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Calo, Vincenzo
Lopez, Luigi
Pesce, Giannangelo
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 head-to-head coupling process.The change in the selectivity is probably due to the co-ordinative effects of the substrate towards the organometallic species.
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