The First Reaction of Dimethoxycarbene with an Imine
نویسندگان
چکیده
The nucleophilic dimethoxycarbene (DMC; 2) generated by thermal decomposition of 2,5dihydro-1,3,4-oxadiazole derivative 1 in boiling toluene reacts smoothly with N-(9H-fluoren-9-ylidene)-4methylbenzenesulfonamide (7b) to yield carbonimidoate derivative 10. A multi-step reaction pathway, initiated by the attack of DMC onto the C=N bond and followed by the migration of the sulfonyl group (or via a sulfinate anion) is proposed to explain the formation of the final product. In contrast to the formal ketimine 7b, N-benzylidene-4-methylbenzenesulfonamide (7a), a formal aldimine, does not react with DMC under comparable conditions. DOI: https://doi.org/10.1002/hlca.200790185 Posted at the Zurich Open Repository and Archive, University of Zurich ZORA URL: https://doi.org/10.5167/uzh-50666 Accepted Version Originally published at: Mloston, G; Heimgartner, H (2007). The first reaction of Dimethoxycarbene with an imine moiety. Helvetica Chimica Acta, 90(9):1758-1764. DOI: https://doi.org/10.1002/hlca.200790185 Prof. Dr. H. Heimgartner Tel. 044 635 4282 Fax 044 635 6812 e-mail: [email protected] The First Reaction of Dimethoxycarbene with an Imine
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