Barbier‐Type Addition of Alkyl Halides to Aldehydes Promoted by Pentacarbonyliron.

Abstract

Alcohols Alcohols Q 0230Barbier-Type Addition of Alkyl Halides to Aldehydes Promoted by Pentacarbonyliron. -Reaction of perfluorobutyl iodide (I) as well as allylic halides (IV) with aromatic aldehydes (II) in the presence of Fe(CO) 5 proceeds by a Barbier-type addition to furnish the expected secondary alcohols in low to moderate yields. Clearly, the p-methoxy group in aldehyde (IIc) has a deactivating influence, so that low amount of adduct (IIIc) is obtained, and with allylic halides no reaction takes place at all. A different reaction outcome is observed with hexyl iodide, which is carbonylated to furnish dihexyl ketone (IX). -(VASIL'EVA, T. T.; MYSOVA, N. E.; CHAKHOVSKAYA, O. V.; TERENT'EV, A. B.; Russ.