期刊
HELVETICA CHIMICA ACTA
卷 98, 期 4, 页码 462-473出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/hlca.201500057
关键词
-
资金
- National Science Center (PL-Cracow) [Dec-2012/06/A/ST5/00219]
Dihetaryl thioketones react with thiocarbonyl ylides to give 1,3-dithiolanes in high yields. No competitive side reactions of the thiocarbonyl ylides were observed, evidencing the 'superdipolarophilic' character of this less-known group of thioketones. Depending on the type of substituents present in both the thiocarbonyl ylide and the thioketone, formal [3 + 2] cycloadditions occur with complete regioselectivity or with formation of a mixture of both regioisomers. Regioselective formation of the sterically more crowded 1,3-dithiolanes is explained via a mechanism involving stabilized 1,5-biradicals. In systems with less-efficient radical stabilization, e.g., in the case of adamantanethione S-methanide, substantial violation of the regioselectivity was observed as a result of steric hindrance.
作者
我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。
推荐
暂无数据