The Base-catalyzed Condensation of α-Haloaldehydes with Dichloroacetates
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概要
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The reaction of aliphatic α-haloaldehydes with methyl dichloroacetate in the presence of sodium methoxide was carried out. α-Chloroaldehydes afforded 2,4-dichloro-2,3-epoxyalkanoates (<B>5</B>), whereas α-bromoaldehydes gave 2,2-dichloro-3,4-epoxyalkanoate (<B>7</B>). The attempted epoxy-carbonyl rearrangement of <B>5</B> with hydrogen chloride or thionyl chloride failed. The thermal decomposition of methyl 2,4-dichloro-2,3-epoxynonanoate (<B>5c</B>) at 300–400°C afforded methyl 3-chloro-2-oxo-3-nonenoate (<B>9c</B>), and the similar treatment of methyl 2,4-dichloro-4-methyl-2,3-epoxypentanoate (<B>5a</B>) afforded a mixture of methyl 3,4-dichloro-4-methyl-2-oxopentanoate (<B>6a</B>), methyl 3-chloro-4-methyl-2-oxo-3-pentenoate (<B>9a</B>), and methyl 3-chloro-4-methyl-2-oxo-4-pentenoate (<B>10</B>). The treatment of <B>5</B> with thiourea in methanol gave the thiazole derivative (<B>15</B>), but neither sodiomalonate nor sodioacetoacetate reacted with <B>5</B>.
- 公益社団法人 日本化学会の論文
著者
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Tsuboi Sadao
Department Of Applied Chemistry Faculty Of Engineering Okayama University
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Kato Hiroshi
Department Of Applied Biological Chemistry Graduate School Of Agricultural And Life Sciences The Uni
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Wada Satoshi
Department of Applied Chemistry, Tokyo University of Agriculture & Technology,
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Wada Satoshi
Department of Synthetic Chemistry, School of Engineering, Okayama University
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Takeda Akira
Department of Applied Chemistry, Faculty of Engineering, Okayama University
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Kato Hiroshi
Department of Synthetic Chemistry, School of Engineering, Okayama University
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