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A New and Regioselective Synthesis of Aromatic Diazene Derivatives
Neumann, Wilhelm P.,Wicenec, Christian
, p. 2297 - 2301 (2007/10/02)
A new method for the preparation of aromatic diazene derivatives 3a-l, 5, 7a, b, 9 under very mild conditions is described.The reaction of trialkylarylstannanes with nitro-substituted benzenediazonium tetrafluoroborates leads, by strict ipso substitution, to the corresponding diaryldiazenes in satisfactory to high yields.Due to the excellent leaving group quality of the stannyl group azo compounds may be prepared which are not accessible by normal electrophilic azo coupling.The products can be valuable precursors, obtained by reduction of the amines or other derivatizations, for consecutive aromatic compounds.Key Words: Aromatic substitution, electrophilic / Azo compounds, synthesis of / Diazonium compounds, aromatic, coupling reaction of, with trialkylarylstannanes / Trialkylarylstannanes, application of
