Solid-state photolysis of alpha-azidoacetophenones.
Solid-state photolysis of 1 yields 2 in a crystal-to-crystal reaction. The reaction takes place by alpha-cleavage to form a benzoyl and an azido alkyl radical pair. The azido alkyl radicals rearrange into iminyl radicals and N2. The iminyl and benzoyl radicals are held in close proximity within the crystal lattice, which allows them to combine and form 2. X-ray structure analysis, molecular modeling and trapping studies support this mechanism.
Mandel
Sarah M
SM
Department of Chemistry, University of Cincinnati, Cincinnati, Ohio 45221-0172, USA.
Singh
Pradeep N D
PN
Muthukrishnan
Sivaramakrishnan
S
Chang
Mingxin
M
Krause
Jeanette A
JA
Gudmundsdóttir
Anna D
AD