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C-H carbene insertion of alpha-diazo acetamides by photolysis in non-conventional media

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Details

Original languageEnglish
Pages (from-to)5926-5932
Number of pages7
JournalJournal of Organic Chemistry
Volume73
Issue number15
DOIs
Publication statusPublished - 1 Aug 2008
Externally publishedYes
Publication typeA1 Journal article-refereed

Abstract

Light from a mercury vapor high-pressure lamp was used to induce the photolytic decomposition of alpha-diazo acetamides in hexane and in nonconventional media such as water or a film. The corresponding beta- and/or gamma-lactams were obtained in reasonable yields and in some cases with good diastereoselectivities with no need to use a metallic catalyst. Experimental studies on chiral substrates demonstrated the occurrence of insertion with retention of configuration.

Keywords

  • CARBON-HYDROGEN INSERTION, ORGANIC-REACTIONS, AQUEOUS-MEDIA, WOLFF REARRANGEMENT, DIAZOCARBONYL COMPOUNDS, WATER, DECOMPOSITION, ESTERS, DIAZOACETAMIDES, STEREOCHEMISTRY

Field of science, Statistics Finland