Tampere University of Technology

TUTCRIS Research Portal

Pot-economy autooxidative condensation of 2-Aryl-2-lithio-1,3-dithianes

Research output: Contribution to journalArticleScientificpeer-review

Details

Original languageEnglish
Pages (from-to)1948-1958
Number of pages11
JournalJournal of Organic Chemistry
Volume83
Issue number4
DOIs
Publication statusPublished - 16 Feb 2018
Publication typeA1 Journal article-refereed

Abstract

The autoxidative condensation of 2-aryl-2-lithio-1,3-dithianes is here reported. Treatment of 2-aryl-1,3-dithianes with n-BuLi in the absence of any electrophile leads to condensation of three molecules of 1,3-dithianes and formation of highly functionalized α-thioether ketones orthothioesters in 51-89% yields upon air exposure. The method was further expanded to benzaldehyde dithioacetals, affording corresponding orthothioesters and α-thioether ketones in 48-97% yields. The experimental results combined with density functional theory studies support a mechanism triggered by the autoxidation of 2-aryl-2-lithio-1,3-dithianes to yield a highly reactive thioester that undergoes condensation with two other molecules of 2-aryl-2-lithio-1,3-dithiane.

ASJC Scopus subject areas

Publication forum classification

Field of science, Statistics Finland