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

被引：87

作者：

Liu, Q ^{[1
]}

Che, GB ^{[1
]}

Yu, HF ^{[1
]}

Liu, YC ^{[1
]}

Zhang, JP ^{[1
]}

Zhang, Q ^{[1
]}

Dong, DW ^{[1
]}

机构：

[1] NE Normal Univ, Dept Chem, Changchun 130024, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 23期

关键词：

D O I：

10.1021/jo034702t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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-propane-dithiol 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.

引用

页码：9148 / 9150

页数：3

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