Convenient access to bicyclic and tricyclic diazenes.
Heating the tosylhydrazone of an omega-alkenyl ketone or aldehyde to reflux in toluene in the presence of K(2)CO(3) delivered the bicyclic diazene. Irradiation of the diazene converted it to the cyclopropane. This appears to be a generally useful method for the construction of substituted cyclopentanes and cyclohexanes.
Taber
Douglass F
DF
Department of Chemistry, University of Delaware, Newark, Delaware 19716, USA. taberdf@udel.edu
Guo
Pengfei
P
D000447:Aldehydes / Q000737:chemistry; D002625:Chemistry, Organic / Q000379:methods*; D003500:Cyclization; D003517:Cyclopentanes / Q000737:chemistry; D007094:Imides / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D008956:Models, Chemical; D044024:Tetralones / Q000737:chemistry*; D014050:Toluene / Q000737:chemistry
D000447:Aldehydes; D003517:Cyclopentanes; D007094:Imides; D007659:Ketones; D044024:Tetralones; D014050:Toluene; C038867:diazene