Document Type

Journal Article

Department/Unit

Department of Chemistry

Title

Silver triflate catalyzed cyclopropyl carbinol rearrangement for benzo[b]oxepine and 2H-chromene synthesis

Language

English

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.

Keywords

Homogeneous catalysis, Oxygen heterocycles, Rearrangement, Ring expansion, Silver

Publication Date

2015

Source Publication Title

European Journal of Organic Chemistry

Volume

2015

Issue

20

Start Page

4447

End Page

4456

Publisher

Wiley-VCH Verlag

DOI

10.1002/ejoc.201500374

Link to Publisher's Edition

http://dx.doi.org/10.1002/ejoc.201500374

ISSN (print)

1434193X

ISSN (electronic)

10990690

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