DIRECT OBSERVATION OF ALPHA-OXO KETENES FORMED FROM 1,3-DIOXIN-4-ONES AND THE ENOLS OF BETA-KETO-ESTERS

被引:68
作者
FREIERMUTH, B [1 ]
WENTRUP, C [1 ]
机构
[1] UNIV QUEENSLAND,DEPT CHEM,BRISBANE,QLD 4072,AUSTRALIA
关键词
D O I
10.1021/jo00007a008
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The enol forms of beta-keto esters thermolyze to alcohols and alpha-oxo ketenes, which are characterized by low-temperature IR spectroscopy and on warming regenerate the beta-hydroxy-alpha,beta-unsaturated esters. The matrix isolated s-Z and s-E forms of alpha-oxo ketenes are characterized and photochemically converted into other conformers or sites. Matrix photolysis of 2,2,6-trimethyl-1,3-dioxin-4-one gives the s-Z acetylketene initially. Alpha-Oxo ketenes polymerize in the cold and dimerize only at elevated temperatures.
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页码:2286 / 2289
页数:4
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