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Synthesis 2013; 45(6): 773-776
DOI: 10.1055/s-0032-1316860
DOI: 10.1055/s-0032-1316860
paper
α-Carboxy-β-Lactones from Photoinduced Ring Contraction of 3-Diazodihydrofuran-2,4-diones
Weitere Informationen
Publikationsverlauf
Received: 30. November 2012
Accepted after revision: 04. Februar 2013
Publikationsdatum:
14. Februar 2013 (online)
Abstract
β-Lactones were prepared by irradiation of 3-diazodihydrofuran-2,4-diones via Wolff rearrangement proceeding with retention of the configuration of the migrating carbon atom. In the presence of alcohols or thiols, but not amines, the corresponding 3-(alkoxycarbonyl)- or 3-[(alkylsulfanyl)carbonyl]-β-lactones were obtained. 5-Alkyl-3-diazodihydrofuran-2,4-diones gave exclusively trans-3,4-disubstituted β-lactones.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis. Included are experimental details and data for compounds 2–8.
- Supporting Information
-
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