1,2-BIS(PHENYLSULFONYL)ALKENES AS VERSATILE GROUPS IN ORGANIC SYNTHESIS: THE PREPARATION OF ALKYL- AND ARYL-SUBSTITUTED NORBORNADIENES VIA THE DIELS-ALDER CYCLOADDITION - GRIGNARD REACTION - DESULFONYLATION SEQUENCE

Article abstract of DOI:10.1016/S0040-4039(00)99595-9

A synthetic methodology for the preparation of the formal Diels-Alder cycloadducts of alkyl- and aryl-substituted acetylenes which exemplifies the utility of bis(phenylsulfonyl)alkenes 1 in organic synthesis is presented.The procedure entails <4+2>-cycloaddition of (e)-1,2-bis(phenylsulfonyl)-1-chloroethylene (4), grignard reaction and desulfonylation; each step occurs in high yield.