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Synthesis 2007(5): 744-748  
DOI: 10.1055/s-2007-965923
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 12-Oxotetradecano-14-lactam

Yue-Mei Jia, Xiao-Mei Liang, Le Chang, Dao-Quan Wang*
Key Laboratory of Pesticide Chemistry and Application Technology, Department of Applied Chemistry, China Agricultural University, Beijing 100094, P. R. of China
Fax: +86(106)2732219; e-Mail: wangdq@cau.edu.cn;
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Publication History

Received 6 November 2006
Publication Date:
08 February 2007 (online)

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Abstract

12-Oxotetradecano-14-lactam was synthesized in 32% total yield starting from 2-nitrocyclododecanone by Michael addition to acrylamide, followed by Hofmann rearrangement and ring expansion, and Nef reaction. The conditions for the Michael addition of 2-nitrocyclodecanone to acrylamide, Hofmann rearrangement of the addition product, and the ring-expansion reaction were studied. The structures of the target compounds, intermediates, and byproducts were characterized by 1H NMR, 13C NMR, and infrared spectroscopic methods, mass spectrometry, and elemental analysis.

Key words

2-nitrocyclododecanone - Michael addition - ring expansion - 12-nitrotetradecano-14-lactam - 12-oxotetradecano-14-lactam