著者

辻 二郎

出版者

公益社団法人精密工学会

雑誌

精密機械 (ISSN:03743543)

巻号頁・発行日

vol.26, no.304, 1960-05-05

著者

辻 二郎

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.25, no.11, pp.984-998, 1967-11-01 (Released:2011-07-05)

参考文献数

138

被引用文献数

2 1

著者

辻 二郎

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.41, no.7, pp.619-632, 1983-07-01 (Released:2009-11-13)

参考文献数

54

被引用文献数

9 8

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Following reactions of various allylic compounds catalyzed by palladium-phosphine complexes are surveyed. Allyl carbonates react with nucleophiles under neutral conditions at room temperature. Allyl alkenyl carbonates and allyl β-keto esters undergo decarboxylation and regioselective intramolecular allylation to afford allylated ketones. 1, 3-Dienemonoxides react with nucleophiles to give 1, 4-adduct with high selectivity. Palladium-catalyzed cyclization of methyl (E) - 3-oxo-8-phenoxy-6-octenoate gives 3-vinylcyclopentanone-2-carboxylate, which is useful starting material for steroids and jasmonate syntheses. Allyl alkenyl carbonates and allyl β-keto esters are converted to α, β-unsaturated ketones by decarboxylative dehydrogenation in acetonitrile using diphosphine. Allylic compounds are converted to mainly 1-olefins by hydrogenolysis with formates. Allyl carbonates are carbonylated under mild conditions to give β, γ-unsaturated esters. Conjugated dienes are formed from allylic compounds by palladium- catalyzed elimination reaction.