7-Oxabicyclohept-2-ene and Related Materials by Reductive Elimination

Article abstract of DOI:10.1021/jo00222a028

The cycloadduct 1 of furan and (E)-1,2-bis(phenylsulfonyl)ethylene has been converted to various derivatives which in turn have been subjected to sodium amalgam reductive elimination conditions.Some of these procedures constitute useful methods for the preparation of the title olefin.The amalgam reduction of 1 provides modest yields of 7-oxabicyclo<2.2.1>hepta-2,5-diene.The cycloadduct of isobenzofuran and the reactive dienophile was prepared and subjected to analogous reactions.Various reaction steps which compete with reductive elimination have been identified.