Intramolecular cyclisation of substituted phenoxyethanols and related compounds with mercury(II) oxide and iodine
- 1 January 1978
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 6,p. 646-652
- https://doi.org/10.1039/p19780000646
Abstract
Electron-donating substituents have been shown to promote intramolecular cyclisation of 2-phenoxyethanols to form Ar1-5 and Ar2-6 cyclisation products. The meta-iodo-substituent promotes Ar2-6 cyclisation to form 2,3-dihydro-1,4-benzodioxins. The Ar2-6 cyclisation product from 3-phenylpropan-1-ols has been shown to be formed by rearrangement of an Ar1-5 intermediate in which carbon migrates in preference to oxygen. Ar1-6 cyclisation of 3-phenoxypropan-1-ols is shown to occur less readily than the corresponding Ar1-5 cyclisation of 2-phenoxyethanols.Keywords
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