The first example of fluoro-Meinwald rearrangement

摘要

Novel fluorinated norbornadienes were synthesized in up to 95% yield by the base-induced elimination of HNO2 from 5-fluoro-5-nitro-6-arylbicyclo[2.2.1]hept-2-enes prepared, in turn, by the Diels-Alder reaction of b-fluoro-b-nitrostyrenes with cyclopentadiene. The subsequent epoxidation initiated the Meinwald type rearrangement affording 6-arylbicyclo[3.1.0]hex-2-ene-6-carboxylic acid fluorides as individual (1SR,5RS,6RS)-diastereomers. The transformation is the first example of fluoro-Meinwald rearrangement to form the corresponding acyl fluorides.