Dichotomous Reactivity in the Reaction of Triethyl- and Triphenylphosphane HBr Salts with Dimethyl Acetals: A Novel Entry to α-Alkoxy-Functionalized Ylides and General Synthesis of Vinyl Ethers and Alkoxy Dienes

✍ Scribed by Priyabrata Das; James McNulty

• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: English
• Weight: 597 KB
• Volume: 2010
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.201000601

✦ Synopsis

Abstract

The discovery of dichotomous reactivity in the reaction of trialkyl‐ vs. triphenylphosphane HBr salts with acetals allows entry to functionalized α‐methoxy phosphonium salts and a novel process for tertiary phosphane methylation. The new protocol opens a general entry to the synthesis of vinyl ethers and differentially substituted 1,3‐dienes via Wittig reactions of the functionalized ylides derived from the α‐methoxy phosphonium salts.