ISSN:
0009-2940
Keywords:
Thioacetals, semicyclic
;
Carbanions
;
Alkylation
;
Hydroxyalkylation
;
Diastereoselectivity
;
Thiolanes
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19921250720
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