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Generation of a η6-Arene/Cr(Co)3-Complexed Diazonium Ion; Homolytic and Heterolytic Dediazoniation via Metallic π-Bonded Aryl Radicals and Cations

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The reaction of NO+ with o-toluidinechromium tricarbonyl has been studied. Diazotization (attack on N) competes with NO+ attack on the metal and decarbonylation. The Cr(CO)3-complexed diazonium ion is unstable and dediazoniates even at low temperature. The dediazoniation mechanism is predominantly homolytic. Competing heterolytic dediazoniation is observed in highly ionizing, low nucleophilicity solvents such as CF3SO3H (TfOH), FSO3H and CF3 CH2 OH (TFE).

Affiliations: 1: Department of Chemistry Kent State University Kent, OH 44242, U.S.A.


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