observation of 1,3-diketones formation in the reaction of bulky acyl chlorides with methyllithium观察1、3-diketones形成与methyllithium笨重酰氯化物的反应.pdfVIP

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observation of 1,3-diketones formation in the reaction of bulky acyl chlorides with methyllithium观察1、3-diketones形成与methyllithium笨重酰氯化物的反应.pdf

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observation of 1,3-diketones formation in the reaction of bulky acyl chlorides with methyllithium观察1、3-diketones形成与methyllithium笨重酰氯化物的反应

Molecules 2012, 17, 6415-6423; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Observation of 1,3-Diketones Formation in the Reaction of Bulky Acyl Chlorides with Methyllithium Jian Zhang, Nianfa Yang * and Liwen Yang * Key Laboratory of Environmentally Friendly Chemistry and Applications of the Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan 411105, China; E-Mail: zhangjian.507@163.com * Authors to whom correspondence should be addressed; E-Mails: nfyang@ (N.Y.); yangliwen_0519@163.com (L.Y.); Tel.: +86-731-5829-3833 (N.Y.); Fax: +86-731-5829-2251 (N.Y.). Received: 26 March 2012; in revised form: 23 May 2012 / Accepted: 23 May 2012 / Published: 29 May 2012 Abstract: The formation of 1,3-diketones was observed in the reactions of bulky acyl chlorides with methyllithium. The reaction products depend on the steric hindrance around the carbonyl group of the acyl chloride and the electronic effect of the group(s) linked to the carbonyl. When the steric hindrance around the carbonyl group of the acyl chloride is big enough, the 1,3-diketone is the only product. In the case of the moderate hindrance around the carbonyl group of the acyl chloride, a moderate yield of 1,3-diketone is obtained and some tertiary alcohol is generated. When there is no steric hindrance around the carbonyl group of the acyl chloride, the tertiary alcohol is the only product. When the steric hindrance around the