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- Title
Silver Triflate Catalyzed Cyclopropyl Carbinol Rearrangement for Benzo[ b]oxepine and 2 H-Chromene Synthesis.
- Authors
Chan, Philip Wai Hong; Teo, Wan Teng; Koh, Shaun Wei Yong; Lee, Bo Ra; Ayers, Benjamin James; Ma, Dik‐Lung; Leung, Chung‐Hang
- Abstract
An efficient AgOTf-catalyzed (TfO = trifluoromethanesulfonate) cyclopropyl carbinol rearrangement for the synthesis of benzo[ b]oxepines and 2 H-chromenes is reported by starting from 2-[cyclopropyl(hydroxy)methyl]phenols. The reactions proved to be general in scope and furnished a range of the corresponding functionalized oxygen heterocycles. The formation of the benzo-fused six-membered adduct is proposed to result from the ring-contraction of the benzo[ b]oxepine derivative. Control of the product selectivity is achievable by fine-tuning the reaction time. The catalytic synergy between the silver(I) cation and the triflate anion was essential for optimal product yields.
- Subjects
CYCLOPROPYL compounds synthesis; PHENOLS; CATIONS; ANIONS; ORGANIC chemistry research
- Publication
European Journal of Organic Chemistry, 2015, Vol 2015, Issue 20, p4447
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201500374