- Magnesium Salt-Induced Opening of α,β-Epoxy Sulfoxides: A Synthesis of α-Chloro Ketones, α-Alkoxy Ketones, and α,β-Unsaturated Ketones from Carbonyl Compounds through α,β-Epoxy Sulfoxides
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Magnesium chloride in alcohols was found to be effective to promote the opening of α,β-epoxy sulfoxides, giving a variety of compounds such as α-chloro ketones, α-alkoxy ketones, or α,β-unsaturated ketones.The products of the reaction were dependent upon the combination of the substituents on the epoxy group of α,β-epoxy sulfoxides, magnesium salt, solvent, and reaction conditions.Keywords -- α,β-epoxy sulfoxide; epoxide; α-chloro ketone; α-alkoxy ketone; α,β-unsaturated ketone; magnesium chloride
- Satoh, Tsuyoshi,Sugimoto, Atsushi,Yamakawa, Koji
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p. 4632 - 4636
(2007/10/02)
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- A NEW SYNTHESIS OF α,β-UNSATURATED KETONES. ALLYLIC ALKYLATION OF 1-ISOCYANO-1-TOSYLALKENES
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Ketones (1) are homologated to enones 2 by alkylating (introduction of R3) the condensation products 4 (derived from 1 and tosylmethyl isocyanide), followed by acid catalyzed hydrolysis.
- Moskal, Janusz,Leusen, Albert M. van
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p. 2585 - 2588
(2007/10/02)
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- Novel Acylation of Aliphatic Olefins Promoted by Active Zinc Compounds
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It was found that acylation of a variety of aliphatic olefins with acid chlorides is efficiently promoted by active zinc compounds, which were prepared from a Zn/Cu couple and alkyl iodides.The crude product mixtures were subsequently treated with 1 M KOH in methanol or were subjected to catalytic hydrogenation to afford the corresponding α,β-unsaturated or saturated ketones in good to moderate yields.It was also shown that the reaction fully follows the Markovnikov rule.
- Shono, Tatsuya,Nishiguchi, Ikuzo,Sasaki, Manji,Ikeda, Haruhiko,Kurita, Makoto
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p. 2503 - 2505
(2007/10/02)
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