Investigation of selenides of the thiophene and furan series

Abstract

As in the case of alkyl 2-thienyl selenides, replacement of the alkylseleno group to form the corresponding lithium derivative is observed when n-butyllithium acts on alkyl 2-furyl and alkyl 2-selenienyl selenides. The alkylselenide function is also replaced when alkyl 2-thienyl selenides are treated with excess bromine. A scheme of the mechanism for the reaction of alkyl 2-hetaryl selenides with n-butyllithium is proposed. Alkyl 2-furyl selenides undergo the diene synthesis with maleic anhydride to give phthalic anhydride without a selenide function as the final product.