- Behaviour of Arylazo tert-Butyl Sulfides with Ketone Enolates. Competition between SRN1 α-Arylation and Azocoupling Reactions.
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(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.
- Dell'Erba, Carlo,Novi, Marino,Petrillo, Giovanni,Tavani, Cinzia
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p. 325 - 334
(2007/10/02)
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- A VERSATILE SYNTHESIS OF ARYLACETONES FROM ARYL HALIDES AND ACETYLACETONATE
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Reaction of aryl halides with sodium or potassium acetylacetonate in the presence of a copper catalyst affords directly arylacetones resulted from deacetylation of initially formed 3-arylacetylacetones in good yields.
- Sugai, Saburo,Ikawa, Hiroshi,Okazaki, Tokuji,Akaboshi, Sanya,Ikegami, Shiro
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p. 597 - 600
(2007/10/02)
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