Thiiranes reaction with benzyne

Thiiranes react with benzyne in an efficient synthesis of phenyl vinyl sulfides. The reaction is stereospecific, thus producing ds-(phenylthio)stilbene from cis-2,3-diphenylthiirane and trans-(phenylthio)stilbene from fra .v-2,3-diphenylthiirane (Scheme 24) (84TL2679). 

The period 1996-2006 did not appear to contain papers concerned with reactions of thiiranes or thiirenes with benzyne. 

Reaction of benzyne with thiiranes gives phenyl vinyl sulfides in good yields (9 examples, 64-89% yields). The reaction is stereo specific, as shown by the formation of608 from cis-thiirane 606, and the corresponding trans vinyl sulfide from the m .y-thiirane. ... 

Benzyne was shown to react with a variety of monocyclic and fused-ring thiiranes to produce vinyl thiophenyl ethers <84TL2679>. Initial reaction gives an intermediate betaine, which abstracts the most acidic (kinetic) ring proton, with concomitant C=C bond formation and C—S bond scission, to give excellent yields of products (illustrated for (2) in Scheme 3). The stereochemistry of the starting thiiranes is preserved in the product vinyl sulfides. 

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