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Aromatic Fluorine as a Chemical Label for Detecting Reaction Mechanism
Author(s) -
Suschitzky H.
Publication year - 1967
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.196705961
Subject(s) - aminolysis , fluorine , chemistry , aryl , aryl radical , diazo , decomposition , combinatorial chemistry , mechanism (biology) , thermal decomposition , hydrolysis , reaction mechanism , organic chemistry , photochemistry , catalysis , philosophy , alkyl , epistemology
This article explains how nucleophilically activated fluorine can be used for the detection of ion‐pair formation during the decomposition of various aryl radical generators. Thus a concurrent dual mechanism for the breakdown of certain aryl radical sources can be experimentally demonstrated by fluorine labeling. The bearing of this information on the mechanism of diazo coupling is also discussed. In addition, labeling with aromatic fluorine is applied to the thermolysis of aryl azides, the aminolysis of 3‐aryl‐4‐bromosydnones, and the hydrolysis of 3‐arylsydnone imines. Finally some mechanistic problems are posed which may possibly be solved by this labeling technique.