Activation of the C[BOND]F Bond: Transformation of CF3N[DOUBLE BOND]N- into 5-Azidotetrazoles


  • The financial support of the NSF (Grant CHE0315275), ONR (Grant N00014-021-0600), and DTRA (HDTRA 1-07-1-0024) is gratefully acknowledged. The Bruker (Siemens) SMART APEX diffraction facility was established at the University of Idaho with the assistance of the NSF-EPSCoR program and the M. J. Murdock Charitable Trust, Vancouver, WA (USA)


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N&Ns: The C[BOND]F bond of trifluoromethylazoalkanes, in the presence of a hydrogen at the α carbon, is activated under basic conditions to form a difluoromethylene intermediate with a conjugated double bond, which is transformed in good yield to the corresponding 5-azido-(1-dialkylimino)tetrazole by reaction with NaN3.