Heterocyclic photochemistry in contrast with carbon behavior. Regioselective photochemical rearrangement of an azacyclohexadienone: mechanistic and exploratory organic photochemistry.
The Type-A photochemistry of cyclohexadienones is well-studied and follows a well-established mechanistic pathway. One early example is the rearrangement of santonin to lumisantonin. Another example is the rearrangement of 4,4-diphenylcyclohexa-1,5-dienone. Remarkably, replacement of one carbon by nitrogen alters the reaction course to give a regioselective phenyl migration.
Zimmerman
Howard E
HE
Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53706, USA. zimmerman@chem.wisc.edu
Shorunov
Sergey
S
D001372:Aza Compounds / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry*; D015394:Molecular Structure; D010777:Photochemistry; D013237:Stereoisomerism
D001372:Aza Compounds; D006571:Heterocyclic Compounds; D002244:Carbon