Carbon-Carbon Bond Cleavage of. ALPHA.-Substituted Benzoins by Retro-Benzoin Condensation; A New Method of Synthesizing Ketones.

…, Y Okumura, K IWAMOTO, T HIGASHINO

Index: Miyashita, Akira; Suzuki, Yumiko; Okumura, Yoko; Iwamoto, Ken-Ichi; Higashino, Takeo Chemical and Pharmaceutical Bulletin, 1998 , vol. 46, # 1 p. 6 - 11

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Citation Number: 19

Abstract

When α-benzylbenzoin (3a, α-benzyl-α-hydroxybenzyl phenyl ketone) was treated with potassium cyanide (1) in N, N-dimethylformamide at 80° C for 1 h, the carbon-carbon bond was cleaved, resulting in the formation of deoxybenzoin (4a, benzyl phenyl ketone) and benzaldehyde (2a). This carbon-carbon bond cleavage proceeds through a retro-benzoin condensation mechanism. This mothod of synthesizing ketones was applied to several α- ...