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C,C‐Verknüpfungen mit Schwefel‐stabilisierten Carbanionen, 2 [1] Reaktionen des 2‐(Methylthio)thiolan‐Carbanions mit Elektrophilen [2]
Author(s) -
Böge Askan,
Brunck JörgStephan,
Schwär Gerhard,
Voß Jürgen
Publication year - 1992
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19921250720
Subject(s) - carbanion , chemistry , medicinal chemistry , electrophile , deprotonation , benzonitrile , ketone , butyllithium , alkyl , organic chemistry , ion , catalysis
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.