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Title: Silver triflate catalyzed cyclopropyl carbinol rearrangement for benzo[b]oxepine and 2H-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
Keywords: DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis
Issue Date: 2015
Source: Chan, P. W. H., Teo, W. T., Koh, S. W. Y., Lee, B. R., Ayers, B. J., Ma, D.-L., et al. (2015). Silver triflate catalyzed cyclopropyl carbinol rearrangement for benzo[b]oxepine and 2H-chromene synthesis. European journal of organic chemistry, 2015(20), 4447-4456.
Series/Report no.: European journal of organic chemistry
Abstract: An efficient AgOTf-catalyzed (TfO = trifluoromethanesulfonate) cyclopropyl carbinol rearrangement for the synthesis of benzo[b]oxepines and 2H-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.
ISSN: 1434-193X
DOI: 10.1002/ejoc.201500374
Rights: © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Fulltext Permission: none
Fulltext Availability: No Fulltext
Appears in Collections:SPMS Journal Articles

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