Neighbouring-group participation by phenolate in the opening of an epoxide ring
- 1 January 1977
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 7,p. 917-918
- https://doi.org/10.1039/p29770000917
Abstract
o-(2,3-Epoxypropyl) phenol has been detected by n.m.r. spectroscopy as an intermediate in the reaction of o-allylphenol with m-chloroperbenzoic acid to yield 2,3-dihydro-2-hydroxymethylbenzofuran. An impure sample of o-(2,3-epoxypropyl)phenol was isolated and the kinetics of its conversion into 2,3-dihydro-2-hydroxymethyl-benzofuran in aqueous solution were studied. The rate shows a sigmoid dependence on pH and is proportional to the concentration of o-(2,3-epoxypropyl)phenolate.Keywords
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