C,C‐Verknüpfungen mit Schwefel‐stabilisierten Carbanionen, 2^[1] Reaktionen des 2‐(Methylthio)thiolan‐Carbanions mit Elektrophilen^[2]

Abstract

C,C Coupling with Sulfur‐Stabilized Carbanions, 2 [1] . – Reactions of the 2‐(Methylthio)thiolane Carbanion with Electrophiles [2] The „semicyclic” thioacetal 2‐(methylthio)thiolane ( 4 ) is easily prepared from thiolane (tetrahydrothiophene). It is readily deprotonated by butyllithium to give the lithium derivative 5 , which reacts with alkyl halides, saturated and α,β‐unsaturated carbonyl compounds, and benzonitrile to form the alkyl derivatives 6 , carbinols 7 , allyl alcohols 8 , and – after hydrolysis – the ketone 9 . The diastereoselectivity of the C,C coupling reaction is discussed.