- Rongalite and base-promoted cleavage of disulfides and subsequent Michael addition to α,β-unsaturated ketones/esters: an odorless synthesis of β-sulfido carbonyl compounds
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A highly practical method to access β-sulfido carbonyl compounds was developed, which could be conducted without any expensive reagent, special apparatus/technique, and no requirement of metal catalysts. β-Sulfido carbonyl compounds were formed at room temperature, in short time and with high chemoselectivity in good to excellent yields. A plausible mechanism for the role of Rongalite, as a promoter for the cleavage of disulfides generating thiolate anions that then undergo facile thia-Michael addition to α,β-unsaturated ketones and esters is proposed.
- Guo, Wenxue,Lv, Guangshu,Chen, Jiuxi,Gao, Wenxia,Ding, Jinchang,Wu, Huayue
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supporting information; experimental part
p. 2297 - 2300
(2010/06/16)
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- The Addition of 1-Lithio-1-(phenylthio)alkanes to 2-(N-Methylanilino)acrylonitrile: An Easy Access to 3-(Phenylthio)ketones and 2-Enones
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A simple and versatile strategy for the synthesis of the title compounds is described.The key-step consists in the addition of 1-lithio-1-(phenylthio)alkanes to 2-(N-methylanilino)acrylonitrile, the nucleophilic phenylthioalkylation of an enol-cation equivalent.Alkylation of the adducts and hydrolysis give 3-(phenylthio)ketones, which can be isolated, or without further purification can be transformed into 2-enones via the well known oxidation-elimination procedure.These reactions are possible with allylic derivatives too, therefore the homologous vinylic compoundscan be prepared by the same way.Pyrolysis of the 1-lithioaminonitriles formed within the first step gives aminonitriles of cyclopropanones via cyclization.
- Ahlbrecht, Hubertus,Ibe, Marcellinus
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p. 210 - 214
(2007/10/02)
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