Time-resolved IR detection and study of an iminooxirane intermediate.
[reaction: see text] Iminooxirane 4 has been generated by the reaction of phenylchlorocarbene (2) with phenyl isocyanate (3) and studied by nanosecond time-resolved infrared spectroscopy. Iminooxirane 4 (1830 cm(-1)) isomerizes to alpha-lactam 5 (1880 cm(-1)) at an observed rate of 3 x 10(4) s(-1). Peak assignments were confirmed by a combination of B3LYP calculations and isotopic labeling. An acyclic transition state was found computationally for the isomerization reaction.
Cohen
Andrew D
AD
Department of Chemistry, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland 21218, USA.
Showalter
Brett M
BM
Toscano
John P
JP