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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
Author(s) -
Das Priyabrata,
McNulty James
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000601
Subject(s) - phosphonium , chemistry , reactivity (psychology) , alkoxy group , wittig reaction , organic chemistry , medicinal chemistry , ylide , alkyl , medicine , alternative medicine , pathology
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.