THIAZOLYLMETHYLENETRIPHENYLPHOSPHORANE AND ITS BENZO DERIVATIVE: STABLE AND PRACTICAL WITTIG REAGENTS FOR THE SYNTHESIS OF VINYLTHIAZOLES AND VINYLBENZOTHIAZOLES. TWO-CARBON HOMOLOGATION OF ALDEHYDES.

Article abstract of DOI:10.1016/S0040-4020(01)90345-X

The title thiazolyl phosphorane is a stable yet quite reactive Wittig-type reagent which uppon reaction with various aldehydes affords vinylthiazoles, mainly or exclusively as E-isomers, in very good yields.Also the benzothiazolyl phosphorane derivative, unlike a literature report, prove to react with aldehydes.Vinylthyazoles subjected to formyl deblocking from thiazole nucleous afford two-carbon homologated satured aldehydes.As an example, one of these vinylthiazoles, viz. the β-phenyl derivative 8f, proves to add n-butyl lithium cuprate to give after the formyl deblocking 3-phenylheptanal.