Abstract
The stereochemistry of the pyrolysis of S-alkyl-N- p-tosylsulphilimines was investigated with both the erythro and threo isomers of S-phenyl-S-1-phenyl-2, 2-phenylmethoxy-1-ethyl-N-benzene-sulphonylsulphilimine I E and I T. Pyrolyses revealed that I E gives only trans-1-methoxystilbene V T in nearly quantitative yield while a mixture of 5·5% trans-V T and 94·5% cis-V C are formed from I T. The kinetics of the reactions of both I E and I T obey a good 1st order rate equation. Pyrolysis is considered to proceed via a concerted cis elimination involving a five membered cyclic transition state.
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