Transformation of sulfide linkages to carbon-carbon double bonds. Syntheses of [2.2] metaparacyclophane-1, 9-dienes

V Boekelheide, PH Anderson…

Index: Boekelheide,V. et al. Journal of the American Chemical Society, 1974 , vol. 96, # 5 p. 1558 - 1564

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Citation Number: 58

Abstract

Abstract: The two-step reaction sequence of a Stevens rearrangement followed by a Hofmann elimination provides a convenient synthetic route for transforming 2, l l-dithia [3.3] metaparacyclophanes to [2.2] metaparacyclophane-l, 9-dienes. The requisite 2, l l-dithia [3.3] metaparacyclophanes are readily available in good yield by the condensation of m- xylylene dibromides with p-xylylene dimercaptans or, alternatively, by the condensation of ...