Generation and Reactivity of N,N-Dimethylaminobenzotriazolylcarbene a New Nucleophilic Carbene

Article abstract of DOI:10.1002/jhet.5570330662

N,N-Dimethylaminobenzotriazolylcarbene (5) reacted with phenyl isocyanate in a [1+2+2] cycloaddition and then with nucleophiles to generate various hydantoins 10 in a one-pot procedure. It was also found that this novel carbene reacted with trans-dibenzoylethylene (11) in a [1+4] cycloaddition, generating 2-dimethylamino-3-benzoyl-5-pbenylfuran (13) and 2-phenyl-3-[benzotriazol-1-y1]-4-benzoylfuran (14) whose structures were confirmed by ¹H-¹³C long range correlations as well as the structure of furan 14 being confirmed by X-ray crystallography.