Synthesis and dienophilic reactivity of 1,2-difluorovinylphenylsulfone

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 cy...

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Bibliographic Details
Published in:Tetrahedron 1997-12, Vol.53 (50), p.17127-17138
Main Authors: De Tollenaere, C., Ghosez, L.
Format: Article
Language:English
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Summary: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 addition-elimination sequences. Products resulting from such an addition-elimination sequence were obtained from representative nucleophilic reagents. ( E) and ( Z)-1,2-difluorovinylphenylsulfones 5 have been efficiently prepared. They yielded Diels-Alder adducts with cyclopentadiene but not with electron-rich dienes.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(97)10126-0