β-Trifluoroacetylvinyl phenyl sulfoxide—synthesis, Diels–Alder reaction and computational study

Recent progress in the use of fluoroorganic compounds in pericyclic reactions

“…b-Trifluoroacetylvinyl sulfones 36a,b, their hydrates 37a,b, 62 and the analogous phenyl sulfoxide 38 and its sulfonium salt 39 63 have been studied as dienophiles (Scheme 18). These species are reactive towards simple dienes under thermal conditions with moderate regio-and stereoselectivities.…”

Synthesis of Fluoroalkyl Vinyl Sulfoxides and their Use in Diels-Alder Reactions

“…a,b-unsaturated sulfoxides are interesting dienophiles in the Diels-Alder reaction and are widely used in synthesis. [1][2][3][4][5] For example, phenyl vinyl sulfoxide (1) has been proposed by Paquette et al 6 as an acetylene equivalent in Diels-Alder cycloadditions. Indeed, the thermal extrusion of phenylsulfenic acid (C 6 H 5 SOH) can occur from the adduct during the condensation of 1 with dienes.…”