Synthesis and reactivity of a fluorinated dienophile

Article abstract of DOI:10.1016/0040-4039(96)01877-1

1-(N,N-diethylcarbamoyloxy-2-fluoro-2-(phenylsulfonyl)-ethene has been prepared and reacted with a variety of dienes to give fluorinated [4+2] cycloadducts. In contrast, the desulfonated equivalent 1-(N,N-diethylcarbamoyloxy)-2-fluoro-E-ethene reacts with cyclopentadiene alone, to give mixtures of [4+2] and [2+2] cycloadducts.