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Time-resolved IR detection and study of an iminooxirane intermediate
Andrew D Cohen1, Brett M Showalter, John P Toscano
1Department of Chemistry, Johns Hopkins University, 3400 North Charles Street, Baltimore, Maryland 21218, USA.
Organic Letters
|January 30, 2004
Abstract:
[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.