The synthesis of dihydrofurobenzodioxins by reaction of tetrachloro-1,2-benzoquinone with some 2,3-diphenylfurans

Abstract

The synthesis of some alkyl-2,3-diphenylfurans and their reaction with tetrachloro-1,2-benzoquinone to afford dihydrofurobenzodioxins are described. 2,3-Diphenyl-, 2,3,5-triphenyl-, and tetraphenyl-furan react in the same manner by a Diels–Alder process utilising the hetero-diene part of the quinone. Steric rather than electronic factors are important in determining which double bond of the furan is utilised as the dienophile.