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Aromatic Claisen Rearrangements of Benzyl Ketene Acetals: Conversion of Benzylic Alcohols to ( ortho ‐Tolyl)acetates
Author(s) -
Burns Jed M.,
Krenske Elizabeth H.,
McGeary Ross P.
Publication year - 2017
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.201601354
Subject(s) - chemistry , claisen rearrangement , sigmatropic reaction , ketene , substituent , alkoxy group , intramolecular force , carroll rearrangement , organic chemistry , medicinal chemistry , alkyl
Claisen rearrangements of benzyl vinyl ethers are much less facile than those of aliphatic allyl vinyl ethers, and their synthetic utility has remained relatively unexplored. A one‐pot procedure is reported for the generation and Claisen rearrangement of benzyl vinyl ethers that contain an activating α‐alkoxy substituent on the vinyl group. A [3,3]‐sigmatropic mechanism was supported by trapping of the intermediate isotoluene in an intramolecular Alder–ene reaction.