Protodediazoniation of Aryldiazonium Fluoroborates by Dimethylformamide [1]

Autor: J. Hodge Markgraf, John R. Cort, Manuel Finkelstein, Raymond Chang, Raymond C. Petersen, Michael H. Lavyne, Sidney D. Ross, C.Michael Moore, J. L. Durant, Andrew W. Gross
Rok vydání: 1997
Předmět:
Zdroj: Tetrahedron. 53:10009-10018
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(97)00343-8
Popis: The protodediazoniation of aryldiazonium fluoroborates can be effected by warm dimethylformamide (DMF). The conversion of 4-nitrobenzenediazonium fluoroborate to nitrobenzene was studied in detail. Products derived from trapping experiments were consistent with a homolytic process. Studies with deuterated DMF established that H atom abstraction occurred from both sites in DMF with a formyl:methyl preference of 3.5:1.0. This mechanism was consistent with bond energies and kinetic isotope effects calculated for the DMF radical cation. © 1997 Elsevier Science Ltd.
Databáze: OpenAIRE