Selective pyrolysis of bifunctional compounds: gas-phase elimination of carbonate-ester functionalities

被引：13

作者：

Al-Azemi, Talal F. ^{[1
]}

Dib, Hicham H. ^{[1
]}

Al-Awadi, Nouria A. ^{[1
]}

El-Dusouqui, Osman M. E. ^{[1
]}

机构：

[1] Kuwait Univ, Dept Chem, Safat 13060, Kuwait

来源：

TETRAHEDRON | 2008年 / 64卷 / 18期

关键词：

online-GC gas-phase pyrolysis; selectivity; carbonate-ester bifunction;

D O I：

10.1016/j.tet.2008.01.002

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Compounds containing both carbonate and ester functionalities were synthesized and then subjected to online-GC gas-phase pyrolysis. The carbonate groups were cleaved selectively in all elimination reactions. The end products of the reaction were found to be affected by the nature of the substrate. The presence of hydrogen and carbonyl substituents on the carbon beta to the carbonate group resulted in further product decomposition through a concerted six-membered transition state. Results from flash vacuum pyrolysis (FVP) and analysis of the GC data indicate that the cleavage of the carbonate group is fast, and that the slower secondary decomposition reactions are independent of the presence of the carbonate group. Spectroscopic analyses of the products are reported. (c) 2008 Published by Elsevier Ltd.

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页码：4126 / 4134

页数：9

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