Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/105560
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.
URI: https://hdl.handle.net/10356/105560
http://hdl.handle.net/10220/25972
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

SCOPUSTM   
Citations 5

12
checked on Aug 31, 2020

WEB OF SCIENCETM
Citations 50

11
checked on Oct 24, 2020

Page view(s) 50

168
checked on Oct 29, 2020

Google ScholarTM

Check

Altmetric


Plumx

Items in DR-NTU are protected by copyright, with all rights reserved, unless otherwise indicated.