The Acid-catalyzed Decomposition of α-Diazo β-Hydroxy Ketones

K Miyauchi, K Hori, T Hirai, M Takebayashi…

Index: Miyauchi, Kazuo; Hori, Kimiaki; Hirai, Tsuguji; Takebayashi, Matsuji; Ibata, Toshikazu Bulletin of the Chemical Society of Japan, 1981 , vol. 54, # 7 p. 2142 - 2146

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Citation Number: 12

Abstract

The proton acid-catalyzed decomposition of 3-aryl-2-diazo-3-hydroxy-1-phenylpropanone (1) gave aryl and hydrogen migration products. The former was the enol-form (2) of 2-aryl-3- phenyl-1, 3-propanedione and the latter was the enol-(3) and keto-form (4) of 1-aryl-3- phenyl-1, 3-propanedione. The product ratios, 2/(3+4), were affected by the catalysts and solvents used. More polar solvents favored the formation of aryl migration products (2). On ...