Stereoselective Two-Step Chemical Preparation of 1,4-Dialkyl-1,4-dimethoxycyclohexa-2,5-dienes

Article abstract of DOI:10.1016/S0040-4020(01)89749-0

The reaction of p-benzoquinone (1) with several organolithium compounds (methyl-, ethyl-, n-butyl-, phenyllithium) led, after hydrolysis with water, to the corresponding crude diols 4, which were successively treated with sodium hydride and methyl iodide yielding the expected 1,4-dialkyl-1,4-dimethoxycyclohexa-2,5-dienes 2a-d in a stereoselective manner.The use of a tandem process with two different organolithium reagents followed by methylation by the same procedure yielded stereoselectively the mixed 1-alkyl-4-alkyl' derivatives 2e,f.