Abstract
α-Acyl-α-benzylsulfonyldiazomethanes (2a-d) have been converted to α-benzylsulfonyl-α-substituted-acetic acids (7a-d) by means of the Wolff rearrangement. Reductive removal of the benzylsulfonyl group of 7b-d can be achieved by the use of sodiumethanol in tetrahydrofuran. α-Benzylsulfonyl-α-substituted-propionic acids (9a-d), prepared from benzyl α-benzylsulfonyl-α-substituted-acetates (3a-d), were also debenzyl-sulfonylated under similar reductive conditions. The overall process, in combination with the Arndt-Eistert synthesis of α-sulfonylacetates from acyl chlorides and benzylsulfonyl-diazomethane (1), provides a new, safe method for the homologation of carboxylic acids.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
