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.
Original language | English |
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Pages (from-to) | 5926-5932 |
Number of pages | 7 |
Journal | Journal of Organic Chemistry |
Volume | 73 |
Issue number | 15 |
DOIs | |
Publication status | Published - 1 Aug 2008 |
Externally published | Yes |
Publication type | A1 Journal article-refereed |
Keywords
- CARBON-HYDROGEN INSERTION
- ORGANIC-REACTIONS
- AQUEOUS-MEDIA
- WOLFF REARRANGEMENT
- DIAZOCARBONYL COMPOUNDS
- WATER
- DECOMPOSITION
- ESTERS
- DIAZOACETAMIDES
- STEREOCHEMISTRY