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Chemoselective thioacetalization with odorless 2-(1,3-dithian-2-ylidene)-3-oxobutanoic acid as a 1,3-propanedithiol equivalent
Canadian Journal of Chemistry Pub Date : 2005-10-01 , DOI: 10.1139/v05-184 Haifeng Yu , Dewen Dong , Yan Ouyang , Qun Liu
Canadian Journal of Chemistry Pub Date : 2005-10-01 , DOI: 10.1139/v05-184 Haifeng Yu , Dewen Dong , Yan Ouyang , Qun Liu
Odorless 2-(1,3-dithian-2-ylidene)-3-oxobutanoic acid (1c) was prepared and investigated in the thioacetalization of carbonyl compounds as a 1,3-propanedithiol equivalent. The results showed that the thioacetalization of various carbonyl compounds 2 with 1c proceeded smoothly and afforded the corresponding dithioacetals 3 in high yields (up to 99%) in the presence of acetyl chloride at room or reflux temperatures. Moreover, the thioacetalization exhibited high chemoselectivity between aldehydes and ketones. Key words: chemoselectivity, 2-(1,3-dithian-2-ylidene)-3-oxobutanoic acid, α-oxo ketene dithioacetal, 1,3-propanedithiol equivalent, thioacetalization.
中文翻译:
用无味的 2-(1,3-dithian-2-ylidene)-3-oxobutanoic 酸作为 1,3-丙二硫醇等价物的化学选择性硫缩醛化
制备了无味的 2-(1,3-dithian-2-ylidene)-3-氧代丁酸 (1c),并在羰基化合物的硫代缩醛反应中作为 1,3-丙二硫醇等价物进行了研究。结果表明,在乙酰氯的存在下,在室温或回流温度下,各种羰基化合物 2 与 1c 的硫代缩醛化反应顺利进行,并以高产率(高达 99%)得到相应的二硫代缩醛 3。此外,硫缩醛化在醛和酮之间表现出高化学选择性。关键词: 化学选择性, 2-(1,3-dithian-2-ylidene)-3-oxobutanoic acid, α-oxo ketene dithioacetal, 1,3-propanedithiol 等价物, thioacetalization。
更新日期:2005-10-01
中文翻译:
![](https://scdn.x-mol.com/jcss/images/paperTranslation.png)
用无味的 2-(1,3-dithian-2-ylidene)-3-oxobutanoic 酸作为 1,3-丙二硫醇等价物的化学选择性硫缩醛化
制备了无味的 2-(1,3-dithian-2-ylidene)-3-氧代丁酸 (1c),并在羰基化合物的硫代缩醛反应中作为 1,3-丙二硫醇等价物进行了研究。结果表明,在乙酰氯的存在下,在室温或回流温度下,各种羰基化合物 2 与 1c 的硫代缩醛化反应顺利进行,并以高产率(高达 99%)得到相应的二硫代缩醛 3。此外,硫缩醛化在醛和酮之间表现出高化学选择性。关键词: 化学选择性, 2-(1,3-dithian-2-ylidene)-3-oxobutanoic acid, α-oxo ketene dithioacetal, 1,3-propanedithiol 等价物, thioacetalization。