首个非硫醇类、无臭的1,3 - 丙二硫醇等效物及其在硫缩醛化反应中的应用。

The first nonthiolic, odorless 1,3-propanedithiol equivalent and its application in thioacetalization.

作者信息

Liu Qun, Che Guangbo, Yu Haifeng, Liu Yingchun, Zhang Jingping, Zhang Qian, Dong Dewen

机构信息

Department of Chemistry, Northeast Normal University, Changchun 130024, P. R. China.

出版信息

J Org Chem. 2003 Nov 14;68(23):9148-50. doi: 10.1021/jo034702t.

DOI:10.1021/jo034702t

PMID:14604400

Abstract

2-[2-Chloro-1-(1-chlorovinyl)allylidene]-1,3-dithiane 1 was synthesized by the chlorination of 3-(1,3)-dithianylidenepentane-2,4-dione 2 using the Vilsmeier-Haack reagent in 99% yield. As a novel nonthiolic, odorless 1,3-propanedithiol equivalent, 1 was investigated in the thioacetalization reaction. Various types of aldehydes and ketones 3 were converted to the corresponding dithianes 4 in the presence of 1 in high yields (79-97%). Moreover, 1 exhibited obvious chemoselectivity between aldehyde and ketone in this thioacetalization reaction. A mechanism for this thioacetalization reaction is proposed.

摘要

采用Vilsmeier-Haack试剂对3-(1,3)-二硫亚基戊烷-2,4-二酮2进行氯化反应，以99%的产率合成了2-[2-氯-1-(1-氯乙烯基)亚烯丙基]-1,3-二硫烷1。作为一种新型的非硫醇类、无气味的1,3-丙二硫醇等价物，对1在硫缩醛化反应中的性能进行了研究。在1的存在下，各种类型的醛和酮3能高产率(79-97%)地转化为相应的二硫烷4。此外，在该硫缩醛化反应中，1在醛和酮之间表现出明显的化学选择性。提出了该硫缩醛化反应的机理。