STUDIES IN ALKYLATION OF 3-METHYL-3-SULFOLENE AND THERMOLYSIS OF RESULTING 2-ALKYL-3-SULFOLENES - CONVENIENT SYNTHESIS OF 1,2-DISUBSTITUTED-1,3-DIENES

Abstract

Various 1,2-disubstituted-1,3-dienes have been synthesised through the alkylation of 3-methyl-3-sulfolene (1) followed by thermolysis of the resulting 2-alkyl-3-methyl-3-sulfolene (3,7). The alkylations with bulky iodides, particularly, containing ethylene ketal or phenyl sulfide moiety yield considerable amounts of rearranged 2-alkyl-3-methyl-2-sulfolene (4). The sulfolenes 3,4 & 7 have been desulfonylated under mild conditions to yield corresponding 1,3-dienes.