- Generation of Benzyne in the Thermal Decomposition of 2-Carboxyphenyl p-Toluenesulfonate
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The scope and the mechanism of the generation of 1,2-dehydrobenzene in the thermal decomposition of 2-carboxyphenyl p-toluenesulfonate and its salts (3) have been studied. 1,2-Dehydrobenzene, which can be trapped with dienic or nucleophilic reagents, is formed in a nonconcerted process with the intermediacy of a species C6H4CO2 (11) (probably benzoxet-2-one).A complex mixture of disalicylide, trisalicylide, and some other polysalicylides is formed, in the absence of trapping agents, by polymerization of this intermediate.
- Luis, Santiago V.,Ferrer, Patrick,Burguete, M. Isabel
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- A Predictive Model for the Decarboxylation of Silver Benzoate Complexes Relevant to Decarboxylative Coupling Reactions
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Decarboxylative coupling reactions offer an attractive route to generate functionalized arenes from simple and readily available carboxylic acid coupling partners, yet they are underutilized due to limitations in the scope of carboxylic acid coupling partner. Here we report that the field effect parameter (F) has a substantial influence on the rate of decarboxylation of well-defined silver benzoate complexes. This finding provides the opportunity to surpass current substrate limitations associated with decarboxylation and to enable widespread utilization of decarboxylative coupling reactions.
- Crovak, Robert A.,Hoover, Jessica M.
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p. 2434 - 2437
(2018/02/28)
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