C-H carbene insertion of alpha-diazo acetamides by photolysis in non-conventional media.
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.
Candeias
Nuno R
NR
Centro de Química-Física Molecular, Institute of Nanosciences and Nanotechnology, 1049-001 Lisboa, Portugal.
Gois
Pedro M P
PM
Veiros
Luis F
LF
Afonso
Carlos A M
CA
D002244:Carbon / Q000737:chemistry*; D003979:Diazonium Compounds / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D010782:Photolysis; D012997:Solvents
D003979:Diazonium Compounds; D012997:Solvents; C030011:carbene; C011752:diazoacetamide; D002244:Carbon; D006859:Hydrogen; D008697:Methane