Please use this identifier to cite or link to this item:
https://hdl.handle.net/1959.11/11592
Title: | Hindered ester formation by Sɴ2 azidation of N-acetoxy-N-alkoxyamides and N-alkoxy-N-chloroamides - novel application of HERON rearrangements | Contributor(s): | Mo, Guoning (author); Glover, Stephen (author)![]() |
Publication Date: | 2002 | DOI: | 10.1039/B111250N | Handle Link: | https://hdl.handle.net/1959.11/11592 | Abstract: | Treatment of N-acetoxy-N-alkoxyamides or N-alkoxy-N-chloroamides with sodium azide in aqueous acetonitrile results in Sɴ2 displacement of chloride and the formation of reactive N-alkoxy-N-azidoamides. The reaction with N-acetoxy-N-benzyloxybenzamide has been studied kinetically (k294 = 2 L mol⁻¹ s⁻¹) and azidation of N-formyloxy-N-methoxyformamide has been modeled computationally at the pBP/DN*//HF/6-31G* level of theory. The anomeric amides N-alkoxy-N-azidoamides decompose intramolecularly and spontaneously to esters and two equivalents of nitrogen. This extremely exothermic process facilitates the formation, in excellent yields, of highly hindered esters. | Publication Type: | Journal Article | Source of Publication: | Journal of the Royal Chemical Society: Perkin Transactions 2 (10), p. 1728-1739 | Publisher: | Royal Society of Chemistry | Place of Publication: | United Kingdom | ISSN: | 1364-5471 1472-779X |
Fields of Research (FoR) 2008: | 030505 Physical Organic Chemistry | Socio-Economic Objective (SEO) 2008: | 970103 Expanding Knowledge in the Chemical Sciences | Peer Reviewed: | Yes | HERDC Category Description: | C1 Refereed Article in a Scholarly Journal |
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Appears in Collections: | Journal Article |
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