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Deprotonation of organic radical cations. Chemical evidence for proton transfer between 9,10‐dihydroanthracence radical cations and superoxide radical anions
Author(s) -
Akaba Ryoichi,
Iwasaki Mitsuru,
Matsumura Tsuyoshi,
Kamata Masaki,
Itoh Hiroki
Publication year - 1996
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/(sici)1099-1395(199603)9:3<187::aid-poc764>3.0.co;2-1
Subject(s) - chemistry , photochemistry , deprotonation , anthracene , radical ion , anthrone , tetrafluoroborate , electron transfer , proton coupled electron transfer , oxygenation , medicinal chemistry , ion , organic chemistry , catalysis , ionic liquid , ecology , biology
Photoinduced electron‐transfer oxygenation of 9,10‐dihydroanthracene was carried out with 2,4,6‐triphenylpyrylium tetrafluoroborate (TPP) and 9,10‐dicyanoanthracene (DCA) as sensitizers. The time course of the oxygenation products was studied, and the results showed that anthrone was formed as a primary product in the DCA‐sensitized oxygenation whereas in the TPP‐sensitized oxygenation anthracene was the primary, major product which under the reaction conditions was converted to anthrone. A mechanism involving proton transfer in the radical ion pair consisting of 9,10‐dihydronathracene radical cation and superoxide radical anion, which cannot occur in the TPP‐sensitized oxygenation, was proposed to rationalize the difference in the product distribution in the two sensitized oxygenation reactions.