Diels-Alder Reactions With Unsaturated Sulfoxides. Reactions of (Z)-3-Phenylsulfinylprop-2-Enoic Acid and Methyl-Ester With Furan, 1,3-Diphenylisobenzofuran and Anthracene

Abstract

Methyl (Z)-3-phenylsulfinylprop-2-enoate undergoes Diels -Alder reactions with furan, 1,3-diphenylisobenzofuran and anthracene but chemical and stereochemical courses of the reactions are very dependent upon reaction conditions. Thus, with furan, cis,endo - and cis,exo - adducts are formed exclusively; with 1,3-diphenylisobenzofuran cis,endo - and cis,exo -adducts are formed at low temperatures, whilst the corresponding trans-adducts are formed upon heating; with anthracene where high temperatures are required for condensation cis- and trans-adducts arise together with products from further thermal reactions.