PURPOSE: To obtain an alcohol in high selectivity useful as synthetic intermediate, for plant protective derivatives, by reacting an epoxide with a nucleophilic compound containing a labile hydrogen in the presence of a specific metal complex catalyst.
CONSTITUTION: An epoxide of formula I (R is an organic residue) is reacted with a compound of the formula ZH containing a labile hydrogen (e.g. an alcohol, a phenol, a primary amine or a carboxylic acid) in the presence of a catalyst to give an alcohol of formula II or III, wherein a metal complex of formula IV ((x) is 1 or 2; M is tin, lead or cadmium) is used as the catalyst to give an alcohol of formula III in high stereoselectivity. Use of the metal complex makes it possible to increase the yield and the selectivity for the opening of the epoxide ring as distinct from its isomerization to a carbonyl derivative and/or its polymerization. The metal complex is obtained by electroreduction of Co2(CO)8 in an organic solvent medium in a cell in which the anode consists of the metal M, and the complex when (x) is 2 is novel.
ANDORE MORUTOROO
FURANSHISU PUTEI
ANRI SAMEN