Iron pentacarbonyl assisted photochemical route to 2,5- and 2,6-divinyl-substituted 1,4-benzoquinones from 1-ene-3-ynes

Abstract

Photochemical reaction between the enynes, (Z)-1-methoxybut-1-ene-3-yne, 1 or isopropenyl acetylene, 2 with CO in presence of Fe(CO)5 yields the 2,6- and 2,5-divinyl-substituted 1,4-benzoquinones: 2,6-bis{(Z)-2-methoxyvinyl}-1,4-benzoquinone (3, 42%), 2,5-bis{(Z)-2-methoxyvinyl}-1,4-benzoquinone (4, 31.5%), [{η2,η2:2,6-di(prop-1-en-2-yl)-1,4-benzoquinone}tricarbonyliron] (5, 45%), and {η2,η2:2,5-di(prop-1-en-2-yl)-1,4-benzoquinone}tricarbonyliron] (6, 65%).