(E)- or (Z)-3-arylsulfinylpropenoates have been reacted with several organometallic rea gents. Grignard reagents were found to promote only the complete substitution of the arylsulfinyl group in good yields up to 92%. The reaction followed a stereochemical course of retention of configuration with high values of stereospecificity (up to 99%) in most cases. The observations made are discussed in the light of current views concerning nucleophilic substitution at a vinyl carbon atom. The addition-elimination pathway is considered valid, whereas a route involving the formation of a sulfurane as an intermediate, followed by a ligand coupling, is considered less likely.
Stereospecific cross-coupling reactions of 3-arylsulfinylpropenoates with organometallic reagents
TORTORELLA, Paolo
1996-01-01
Abstract
(E)- or (Z)-3-arylsulfinylpropenoates have been reacted with several organometallic rea gents. Grignard reagents were found to promote only the complete substitution of the arylsulfinyl group in good yields up to 92%. The reaction followed a stereochemical course of retention of configuration with high values of stereospecificity (up to 99%) in most cases. The observations made are discussed in the light of current views concerning nucleophilic substitution at a vinyl carbon atom. The addition-elimination pathway is considered valid, whereas a route involving the formation of a sulfurane as an intermediate, followed by a ligand coupling, is considered less likely.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
