CYCLOCONDENSATION OF OXALYL CHLORIDE WITH 1,2-GLYCOLS

被引:42
作者
IIDA, T [1 ]
ITAYA, T [1 ]
机构
[1] KANAZAWA UNIV,FAC PHARMACEUT SCI,KANAZAWA,ISHIKAWA 920,JAPAN
关键词
D O I
10.1016/S0040-4020(01)81546-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Oxalyl chloride reacts with a wide range of acyclic 1,2-glycols 1 in the presence of triethylamine to produce 1,3-dioxolan-2-ones 3 together with 1,4-dioxane-2,3-diones 2. Ethylene glycol (1d), monosubstituted ethylene glycols 1e, j-1, and erythro-1,2-disubstituted ethylene glycols 1f, m,o provide the cyclic carbonates 3 as the minor products, while the threo-compounds 1g, i, n,p,q and pinacol (1h) afford 3 as the main products. The formation of 3 may be rationalized in terms of stereoelectronically controlled cleavage of the conjugate base 17- of the tetrahedral intermediates. The rate for the conformational change of 17- into 18- and the equilibrium constant between these conformers are proposed to be the major factors affecting the reaction pattern.
引用
收藏
页码:10511 / 10530
页数:20
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