γ-Diphenylphosphinoxy Carbanions: Slow Reacting Analogues of γ -Halocarbanions

Abstract

Carbanion of diphenylphosphinyl ester of 3-hydroxypropyl phenyl sulfone undergoes slow 1,3-intramolecular nucleophilic substitution to give substituted cyclopropane. It can be efficiently trapped by external electrophiles such as aldehydes to produce aldol type anions, which undergo 1,5-intramolecular substitution to give substituted tetrahydrofurans.

Keywords:

• Carbanions
• diphenylphosphinates
• sulfones tetrahydrofurans

Dedicated to Professor Marian Mikołajczyk from the CBMiM PAN in Łódź, Poland, on the occasion of his 70th birthday.

Notes

^a Experiment without aldehyde, BuLi, −75°C to room temperature, THF.

^b Physical and spectral data: see ref. [1].

^c Aldehyde was added 15 s after base.