USE OF SOLID ACIDS TO CATALYZE THE CIS TRANS PHOTOISOMERIZATION OF ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS
USE OF SOLID ACIDS TO CATALYZE THE CIS TRANS PHOTOISOMERIZATION OF ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS
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DOI：
10.1021/jo00197a005
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发表时间：
1984-01-01
影响因子：
3.6
通讯作者：
MIKAGIBALA, A
中科院分区：
文献类型：
--
作者：
CHILDS, RF;DUFFEY, B;MIKAGIBALA, A
在多相酸如铝硅酸盐和Nafion存在下，研究了肉桂酸乙酯、1和2，4-苯基丁-3-烯-2-酮、3和4以及肉桂腈、5和6的溶液的顺/反异构化。当存在非均相酸时，1和2以及3和4的光稳定状态混合物中存在的顺式异构体的比例显著提高，这一发现具有制备意义。这种类型的扰动的光稳定状态的不饱和酯和酮的起源已被详细检查，它表明，所涉及的主要因素是优先吸附的反式与顺式异构体。
The cis/trans isomerization of solutions of ethyl cinnamates, 1 and 2, 4-phenylbut-3-en-2-ones, 3 and 4, and cinnamonitriles, 5 and 6, has been examined in the presence of heterogeneous acids such as the aluminosilicates and Nafion. The proportion of the cis isomer present in the photostationary-state mixtures of 1 and 2 and 3 and 4 is dramatically enhanced when heterogeneous acids are present, a finding that is of preparative significance. The origin of this type of perturbation of the photostationary states of unsaturated esters and ketones has been examined in detail and it is shown that the primary factor involved is the preferential adsorption of the trans vs. the cis isomers.