Ring contraction accompanying nucleophilic substitution in 1,3-dioxan derivatives
- 1 January 1972
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 12,p. 722-723
- https://doi.org/10.1039/c39720000722
Abstract
The reaction of cis-2-phenyl-1,3-dioxan-5-ol with triphenyl phosphine and carbon tetrabromide gives a mixture of diastereomeric 2-phenyl-4-bromomethyl-1,3-dioxolans, whereas only trans-2-phenyl-5-bromo-1,3-dioxan is obtained from the reaction of cis-2-phenyl-1,3-dioxan-5-yl p-toluenesulphonate with lithium bromide.Keywords
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