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Molecules 2012, 17(6), 6415-6423; doi:10.3390/molecules17066415
Article

Observation of 1,3-Diketones Formation in the Reaction of Bulky Acyl Chlorides with Methyllithium

,
*  and *
Key Laboratory of Environmentally Friendly Chemistry and Applications of the Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan 411105, China
* Authors to whom correspondence should be addressed.
Received: 26 March 2012 / Revised: 23 May 2012 / Accepted: 23 May 2012 / Published: 29 May 2012
(This article belongs to the Section Organic Synthesis)
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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 carbonyl group is moderate and an electron-donating group is connected to the carbonyl of the acyl chloride, all three products—ketone, 1,3-diketone and tertiary alcohol—can be isolated from the reaction mixture after long reaction times.
Keywords: acyl chloride; menthylformyl; methyllithium; C2-symmetric; 1,3-diketone acyl chloride; menthylformyl; methyllithium; C2-symmetric; 1,3-diketone
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Zhang, J.; Yang, N.; Yang, L. Observation of 1,3-Diketones Formation in the Reaction of Bulky Acyl Chlorides with Methyllithium. Molecules 2012, 17, 6415-6423.

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