DIENE-DIENOPHILE DUAL REACTIVITY OF CONJUGATED VINYL SULFINES

The discovery of a new and facile synthesis of alpha,beta-unsaturated thioaldehyde S-oxides has enabled the exploration of the diene-dienoph ile reactivity of these novel heterocumulenes. Unlike some previous re ports, the addition of (Z)-beta,beta-dimethylvinyl and (Z)-beta-styryl sulfines to either cyclic or acyclic dienes proceeds in a non-stereos pecific manner, yielding three stereoisomers. In contrast, the latter sulfine reacts as a diene with norbornene and other dienophiles to giv e a single product.