Tetrahedron p. 10009 - 10018 (1997)
Update date:2022-08-30
Topics:
Markgraf, J. Hodge
Chang, Raymond
Cort, John R.
Durant Jr., Joseph L.
Finkelstein, Manuel
Gross, Andrew W.
Lavyne, Michael H.
Moore, W. Michael
Petersen, Raymond C.
Ross, Sidney D.
The protodrdiazoniation 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.
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