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

Abstract

The Diels–Alder reaction of sulfoxide 2 with 1,3-dienes in CH₂Cl₂ afforded the corresponding CF₃-containing mono- and polycycloadducts. In the case of the reaction of sulfoxide 2 and sulfonium salt 10 with cyclopentadiene, a mixture of four diastereomers was formed. The rotational potential energy surface (PES) of reagents 2, 10 was calculated and gave three minimum energy conformations with SO, Ph or the lone pair synperiplanar to the carbon–carbon double bond.