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

Nuno R. Candeias, Pedro M. P. Gois, Luis F. Veiros, Carlos A. M. Afonso

Research output: Contribution to journalArticleScientificpeer-review

34 Citations (Scopus)

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 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

Keywords

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

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