Thermal cycloaddition of N-arylmaleimides to phenols: the convenient synthesis of bicyclo[2.2.2]oct-2-en-5-one and tricyclo[3.3.0.02,8]octan-2-one derivatives from phenols
- 1 January 1987
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 5,p. 1147-1151
- https://doi.org/10.1039/p19870001147
Abstract
Monohydric phenols undergo 2,5-thermal cycloaddition of N-substituted maleimides to give bicyclo[2.2.2]oct-2-en-5-ones. Homopolymers of the maleimides are also concurrently formed, except in the case of N-(2,6-dimethylphenyl)maleimide: this is the preferred addend and gave a 63% yield of the 2,5-adduct as a mixture of exo and endo isomers. U.v. irradiation in acetone of the diester (16) derived from the endo adduct of phenol and N-phenylmaleimide gave the tricyclo[3.3.0.02,8]octan-3-one (17) in quantitative yield.This publication has 0 references indexed in Scilit: