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Photosensitized Electron‐Transfer Reactions of 1‐Isopropylidene‐2‐methylene‐3,3‐diphenylcyclobutane − [4 + 4] Cycloaddition and Cyclodimerization Initiated by a Buta‐1,3‐diene Radical Cation Functionality
Author(s) -
Ikeda Hiroshi,
Aburakawa Nozomi,
Tanaka Futoshi,
Fukushima Takanori,
Miyashi Tsutomu
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200109)2001:18<3445::aid-ejoc3445>3.0.co;2-q
Subject(s) - chemistry , cycloaddition , methylene , photochemistry , adduct , diene , electron transfer , radical ion , medicinal chemistry , organic chemistry , catalysis , ion , natural rubber
The 9,10‐dicyanoanthracene‐photosensitized (DCA‐photosensitized) electron‐transfer reaction of 1‐isopropylidene‐2‐methylene‐3,3‐diphenylcyclobutane ( 3 ) gives a mixture of the [4 + 4] DCA adduct ( 5 ) and two [4 + 4] cyclodimers ( syn ‐ 6 and anti ‐ 6 ), demonstrating that 3 · + functions as a buta‐1,3‐diene radical cation with its SOMO in a mainly localized state.