Novel pathways for oxygen insertion into unactivated C-H bonds by dioxiranes. Transition structures for stepwise routes via radical pairs and comparison with the concerted pathway

Journal of Organic Chemistry

Volumn 68, Issue 3, 2003, Pages 811-823

  Freccero, Mauro ^a   Gandolfi, Remo ^a   Sarzi Amadè, Mirko ^a   Rastelli, Augusto ^b  

^a UNIVERSITY OF PAVIA   (Italy)

^b UNIVERSITY OF MODENA AND REGGIO EMILIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

FREE RADICALS; HYDROGEN BONDS; PROBABILITY DENSITY FUNCTION;

RADICAL PAIRS;

ALCOHOLS;

ACETONE; ALCOHOL; BUTANE; CARBON; CARBONYL DERIVATIVE; ETHYLENE OXIDE DERIVATIVE; HYDROGEN; METHANE; OXYGEN;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENERGY; ENTHALPY; ENTROPY; GEOMETRY; OXIDATION;

EID: 0037423178     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0266184     Document Type: Article

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62. 2b A referee suggested that reaction of secondary C-H bond could represent an artifact due to the onset of radical DMD decomposition over the long reaction times. As a rule, e.g., reactions of DMD with 1,2-dimethylcyclohexanes and decalins, only attack at the tertiary C-H was observed.
63. acetone = 22.24.
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