Selectivity in the allylic substitutions with organometallics through neighboring coordination. 2-(Allyloxy) benzothiazoles as SN2'electrophiles for regio-and …

…, L Lopez, G Pesce, A Calianno

Index: Calo, Vincenzo; Lopez, Luigi; Pesce, Giannangelo; Calianno, Antonia Journal of Organic Chemistry, 1982 , vol. 47, # 23 p. 4482 - 4485

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Citation Number: 16

Abstract

Results The addition of an organomagnesium compound at 0" C to a THF solution of 2- (allyloxy) benzothiazole 2a-d in the presence of stoichiometric amount of copper (1) bromide added immediately before the addition of the Grignard reagent afforded in high yields CC coupling products deriving exclusively from an SN2'-type substitution independently of the bulkiness of substituents borne by the allylic framework as depicted in Scheme 11. The ...