Synthesis and dienophilic reactivity of 1,2-difluorovinylphenylsulfone

✍ Scribed by C. De Tollenaere; L. Ghosez

• Book ID: 104208205
• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 621 KB
• Volume: 53
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(97)10126-0

✦ Synopsis

1,2-Difluorovinylphenylsulfone 5 was conveniently prepared in three steps from chlorotrifluoroethylene. Both E and Z isomers of 5 gave excellent yields of [4+2] cycloadducts with cyclopentadiene. The E isomer reacted with high kinetic exo selectivity. 1,2-Difluorovinylphenylsulfone 5 did not give cycloadducts with highly polar and reactive dienes. Only complex mixtures were obtained. This was assigned to competitive pathways resulting from additionelimination sequences. Products resulting from such an addition-elimination sequence were obtained from representative nucleophilic reagents.