State-dependent photochemistry of highly fluorinated bicyclo[4.2.0]octa-2,4-dienes
作者： Bryan E. Roberts , Glenn D. Goldman , David M. Lemal
DOI: 10.1016/S0022-1139(00)80220-1
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摘要: Abstract A series of 1,2,3,4,5,6-hexafluorobicyclo[4.2.0]octa-2,4-dienes was subjected to direct irradiation with ultraviolet light and triplet sensitization. While all the dienes cyclized smoothly upon tricyclo[4.2.0.0 2,5 ]oct-3-enes, their behavior when sensitized strongly dependent substituents in 7- 8-positions. Responses included no reaction, cyclization tricyclooctene, fragmentation hexafluorobenzene plus olefin. Fragmentation occurred only geminal chlorines were present at 7-position. This observation is consistent view that four-membered ring opens homolytically C 6 C 7 bond, if sufficient stabilization available for a radical center
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