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Dual reactivity of imidic carbonyl ylides in Rh(II)-catalyzed reactions of alpha-diazocarbonyl compounds with succinimide


Nikolaev, Vsevolod; Hennig, Lothar; Heimgartner, Heinz; Schulze, Bärbel; Nikolaev, Valerij (2006). Dual reactivity of imidic carbonyl ylides in Rh(II)-catalyzed reactions of alpha-diazocarbonyl compounds with succinimide. Tetrahedron Letters, 47(15):2643-2647.

Abstract

Stabilization of imidic carbonyl ylides derived from alpha-diazocarbonyl compounds and succinimide occurs in two different ways: ylides from diazoesters experience a [1,4]-hydrogen shift to produce the corresponding O-alkylimidates while their analogues with at least one acyl group undergo [1,5]-electrocyclization yielding 1,3-dioxoles.

Abstract

Stabilization of imidic carbonyl ylides derived from alpha-diazocarbonyl compounds and succinimide occurs in two different ways: ylides from diazoesters experience a [1,4]-hydrogen shift to produce the corresponding O-alkylimidates while their analogues with at least one acyl group undergo [1,5]-electrocyclization yielding 1,3-dioxoles.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2006
Deposited On:22 May 2012 07:02
Last Modified:05 Apr 2016 15:47
Publisher:Elsevier
ISSN:0040-4039
Publisher DOI:https://doi.org/10.1016/j.tetlet.2006.01.155

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