3-甲氧羰基-1-氧薁烷-2-亞胺之合成及其與3-氰-1-氧薁烷-2-酮在鹽基中之互變

The Synthesis of 3-Methoxycarbonyl-1-oxaazlan-2-imine and Its Interconversion with 3-Cyano-1-oxaazulan-2-one in Basic Solution

楊寶旺(Paw-Wang Yang) ； 高世輝(Shih-Hui Kao) ； 劉榮輝(Ron-Fe Liu)

《化學》 62年4期 (1973/12) Pp. 105-110

https://doi.org/10.6623/chem.1973017

摘要

由2-氯（艹卓）酮在鹽基存在下與氰乙酸甲酯的作用合成得m.p. 241°C的黃綠色結晶3-氰-1-氧氧薁烷-2-酮(2)與m.p. 97°C紅褐色結晶的新化合物3-甲氧羰基-1-氧　烷-2-亞胺(4)，其結構依據紅外線、紫外．可見光吸收光譜、核磁共振譜圖、元素分析以及化學性質而推定。上述二化合物在甲醇鈉的甲醇溶液中能互變，鹽基量在1莫耳當量以上時，在溶液中(2)與(4)的存在比例約為1：4。

並列摘要

From the reaction of 2-chlorotropone with methyl cyanoacetate in the presence of sodium methoxide, the greenish yellow crystals 3-cyano-1-oxaazulan-2-one (2), m.p. 241°C, and a new compound of brownish red crystals 3-methoxycarbonyl-1-oxaazulan-2-imine (4), m.p. 97°C, were synthesized. The structure assignment of compound (4) was based on elemental analysis, ir, uv, and nmr spectra studies, as well as chemical method. It was found that compound (2) and (4) could be interconverted in the sodium methoxide solution, and when the methoxide is greater than one molar equivalent, the ratio of compound (2) and (4) in solution is about 1 :4, despite of compound (2) or (4) being used as starting material.