79868-86-3Relevant articles and documents
Behaviour of Arylazo tert-Butyl Sulfides with Ketone Enolates. Competition between SRN1 α-Arylation and Azocoupling Reactions.
Dell'Erba, Carlo,Novi, Marino,Petrillo, Giovanni,Tavani, Cinzia
, p. 325 - 334 (2007/10/02)
(Z)-Arylazo tert-butyl sulfides 1a-i react, in DMSO and at room temperature, with potassium acetone enolate to give good yields of 1-aryl-2-propanones via spontaneous SRN1 dark reactions. α-Phenylation of pincolone and acetophenone enolates by 1a likewise occurs in excellent yields.In agreement with the involvement of an electron-transfer catalyzed chain process, the reaction of the 4-bromo derivative 1n with pinacolone enolate gives mainly the bis-substitution product 13.With azosulfides 1j-m the arylation pathway competes with a base-induced thiol elimination eventually leading, depending on the structure of the azosulfide, to indazoles 8 or 11 and/or to 2-oxopropanal arylhydrazones 9, 10 or 12.
