European journal of organic chemistry

The Effects of Ring Size and Substituents on the Rates of Acid??Catalysed Hydrolysis of Five??and Six??Membered Ring Cyclic Ketone Acetals

JP Knowles, A Whiting

文献索引：Knowles, Jonathan P.; Whiting, Andrew European Journal of Organic Chemistry, 2007 , # 20 p. 3365 - 3368

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被引用次数: 10

摘要

Abstract A series of sterically similar five-and six-membered ring cyclic diol-derived ketone acetals have been prepared and their rates of acid-catalysed hydrolysis examined. The rates of hydrolysis are substantially affected by acetal ring conformational stereoelectronic effects and resonance effects depending upon the substituents on the parent ketone; an A1 mechanism of hydrolysis explains the observed effects.(© Wiley-VCH Verlag GmbH & Co. ...