Temperature-dependent rearrangement of 2-(2-furyl)-2-lithio-1,3-dithiane
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The Department of Chemistry seeks to provide students with a foundation in the fundamentals and application of chemical theories and processes of the lab. Thus prepared they me pursue careers as teachers, industry supervisors, or research chemists in a variety of domains (governmental, academic, etc).
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The Department of Chemistry was founded in 1880.
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1880-present
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- College of Liberal Arts and Sciences (parent college)
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Abstract
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.
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Reprinted (adapted) with permission from The Journal of Organic Chemistry, 43(21); 4235-4236. Doi: 10.1021/jo00415a054. Copyright 1978 American Chemical Society.