Temperature-dependent rearrangement of 2-(2-furyl)-2-lithio-1,3-dithiane

Abstract

<p>In the course of our work directed in the area of the DielsAlder reaction, we required the preparation of compounds such as 1. It was thought the use of 2-(2-furyl)-1,3-dithian (2) as a nucleophilic acylating agent would provide an efficient entry into such a system. The use of lithiated 1,3-dithianes is well known and is the subject of two excellent reviews by Seebach.1,2 Interestingly, the synthesis and use of compound 2 had not previously been recorded in the literature. We wish to report the preparation of 2 and the temperature dependent rearrangement of the anion produced from 2.</p>