94799-39-0Relevant articles and documents
Thermal 2,5-Cycloaddition of N-Arylmaleimides to Phenols
Bryce-Smith, Derek,Gilbert, Andrew,McColl, Ian S.,Yianni, Paul
, p. 951 - 952 (1984)
Phenol undergoes thermal 2,5-cycloaddition of N-phenylmaleimide to give endo- and exo-bicyclo-octenones (3) and (4) respectively, and a homopolymer of the maleimide; use of N-(p-methoxyphenyl)maleimide minimises polymer formation, and gives a combined cycloadduct yield of 60percent in the case of p-cresol.
Thermal Cycloaddition of N-Arylmaleimides to Phenols: the Convenient Synthesis of Bicyclooct-2-en-5-one and Tricyclo2,8>octan-2-one Derivatives from Phenols
Bryce-Smith, Derek,Gilbert, Andrew,McColl, Ian S.,Drew, Michael G. B.,Yianni, Paul
, p. 1147 - 1152 (2007/10/02)
Monohydric phenols undergo 2,5-thermal cycloaddition of N-substituted maleimides to give bicyclooct-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 63percent 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 tricyclo2,8>octan-3-one (17) in quantitative yield.