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- Title
Aromatic Claisen Rearrangements of Benzyl Ketene Acetals: Conversion of Benzylic Alcohols to (ortho-Tolyl)acetates.
- Authors
Burns, Jed M.; Krenske, Elizabeth H.; McGeary, Ross P.
- Abstract
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.
- Subjects
CLAISEN rearrangement; VINYL ethers; ACETAL resins; BENZYL alcohol; ENE reactions; ALLYL ether synthesis
- Publication
European Journal of Organic Chemistry, 2017, Vol 2017, Issue 2, p252
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201601354