The Diels–Alder reactivity of (E)-3-phenylsulfonylprop-2-enenitrile, a cyanoacetylene equivalent

摘要

(E)-3-Phenylsulfonylprop-2-enenitrile undergoes facile Diels–Alder reactions, moderate regioselectivity beingnobserved with several unsymmetrical dienes. Danishefsky’s diene and furfuryl alcohol react regioselectively. Thencycloadducts formed with cyclopentadiene and with anthracene undergo base-catalysed elimination ofnbenzenesulfinic acid to yield α,β-unsaturated nitriles.