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ChemInform Abstract: Generation and Reactivity of N,N-Dimethylaminobenzotriazolylcarbene a New Nucleophilic Carbene.

✍ Scribed by A. R. KATRITZKY; D. CHENG; P. LEEMING; I. GHIVIRIGA; C. M. HARTSHORN; P. J. STEEL

Publisher
John Wiley and Sons
Year
2010
Weight
32 KB
Volume
28
Category
Article
ISSN
0931-7597

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✦ Synopsis

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

-The title carbene (V), generated by deprotonation of salt (III) under mild conditions, affords dimeric products (VI) and (VII). It reacts with Ph-NCO (VIII) and various nucleophiles like H2O and (XII) to give the corresponding hydantoins, e.g. (X) and (XIII), via (1 + 2 + 2) cycloaddition in a one-pot procedure. (1 + 4) cycloaddition of carbene (V) with reactant (XIV) provides furans (XV) and (XVI). The structure of product (XV) is confirmed by X-ray analysis.

-(KATRITZKY, A. R.;

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