Preparation of 2-(Tetrahydrofuran-2′-YL)-l,4-Pentadienes From γ-Allenyl Alcohols via Oxymercuration Followed by Palladium(II)-Medlated all Ylation

Abstract

Intramolecular oxymercurations of γ-hydroxy- or γ-silyloxyallenes yielded α-(tetrahydrofuran-2-yl)vinylmercury intermediates which underwent coupling with allylic halides in the presence of palladium(II) chloride. The yields of the resulting 2-(tetrahydrofuran-2′-yl)-1,4-pentadienes diminished when either the vinylmercury compound or the allylic halide was substituted.