Transformation of sulfide linkages to carbon-carbon double bond. Syntheses of cis-and trans-15, 16-dimethyldihydropyrene and trans-15, 16-dihydropyrene

RH Mitchell, V Boekelheide

Index: Mitchell,R.H.; Boekelheide,V. Journal of the American Chemical Society, 1974 , vol. 96, p. 1547 - 1557

Full Text: HTML

Citation Number: 177

Abstract

Abstract: It is shown that the transformation of sulfide linkages to carbon-carbon double bonds in highly strained molecules can be effected conveniently and in high yield by a reaction sequence of a Stevens rearrangement followed by a Hofmann elimination. This route is of particular advantage for preparing cyclophane derivatives since the medium- sized ring sulfides required as starting materials are easy to prepare. When m-xylylene ...