118133-43-0Relevant articles and documents
Regioreversed Nucleophilic Substitution of 2-(Allyloxy)benzothiazole by Allylic Grignard Reagents. A Regioselective Synthesis of 1,5-Dienes
Calo, Vincenzo,Lopez, Luigi,Pesce, Giannangelo
, p. 1301 - 1304 (1988)
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.