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Mechanistic Studies on the Photogenerated Dienol with α‐Phenyl‐ N‐tert ‐Butylnitrones
Author(s) -
Pan Kai,
Ho TongIng
Publication year - 1997
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.199700037
Subject(s) - chemistry , benzophenone , acetophenone , regioselectivity , cycloaddition , nitroxyl , photochemistry , benzaldehyde , decomposition , thermal decomposition , medicinal chemistry , radical , organic chemistry , catalysis
The mechanism for the photochemical reactions of o ‐methyl‐benzaldehyde ( 1 ), o ‐methyl‐acetophenone ( 2 ) and o ‐methyl‐benzophenone ( 3 ) in the presence of α‐phenyl‐ N ‐ tert ‐butylnitrone (PBN) to the formation of stable nitroxyl radicals 4–6 is studied. The nitroxyl radical product 6 can also be obtained by the thermolysis of benzocyclobutenol with PBN. Thus, the radical products were derived from a novel and regioselective 4+2 cycloaddition of the photogenerated dienol intermediate with PBN.