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Chemiexcitation of an anthraquinone derivative in the thermal cycloreversion of a dewar‐anthraquinone derivative
Author(s) -
Miki Sadao,
Kagawa Hiroyuki,
Yoshida ZenIchi
Publication year - 1992
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/poc.610050206
Subject(s) - chemistry , anthraquinone , photochemistry , anthraquinones , isomerization , adiabatic process , excited state , derivative (finance) , valence (chemistry) , thermal decomposition , singlet state , organic chemistry , atomic physics , thermodynamics , botany , physics , financial economics , economics , biology , catalysis
Abstract Dewar‐anthraquinone (1a) and 1,2,3‐ tri‐tert ‐butyl‐5,8‐Dewar‐anthraquinone (1b) were synthesized. Thermodynamic parameters for their cycloreversion to the corresponding anthraquinones indicate that thermal population of the excited states of the products via non‐adiabatic valence isomerization is energetically feasible. On thermolysis of 1b, the formation of a detectable amount of 1,2,3‐ tri‐tert ‐butyl‐1,4‐Dewar‐anthraquinone (3) was observed. The excited singlet state of 1,2,3‐ tri‐tert ‐butylanthraquinone (2b) produced via the non‐adiabatic process is responsible for the formation of 3.