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RhII-catalyzed reactions of Diazocarbonyl compounds with Dicarboximides


Nikolaev, V V; Heimgartner, H; Linden, A; Krylov, I S; Nikolaev, V A (2006). RhII-catalyzed reactions of Diazocarbonyl compounds with Dicarboximides. European Journal of Organic Chemistry, 2006(20):4737-4746.

Abstract

The reaction of RhII–oxocarbenoids derived from acyclic diazocarbonyl compounds with phthalimide and succinimide proceeds chemoselectively at the oxygen atom of the imidic carbonyl group, giving rise to the intermediate formation of carbonyl ylides. Intramolecular stabilization of these highly reactive species occurs in three different ways, and is controlled by the structure of the 2-oxocarbenoids. Carbonyl ylides from diazo esters mainly experience a [1,4]-hydrogen shift, and in this case, the corresponding O-alkylimidates are formed as the final products. These ylides may also be stabilized by 1,3-dipolar electrocyclization with intermediate formation of an oxirane. Carbonyl ylides with an acyl group in the carbene moiety undergo an intramolecular 1,5-dipolar electrocyclization to produce 1,3-dioxole derivatives.

Abstract

The reaction of RhII–oxocarbenoids derived from acyclic diazocarbonyl compounds with phthalimide and succinimide proceeds chemoselectively at the oxygen atom of the imidic carbonyl group, giving rise to the intermediate formation of carbonyl ylides. Intramolecular stabilization of these highly reactive species occurs in three different ways, and is controlled by the structure of the 2-oxocarbenoids. Carbonyl ylides from diazo esters mainly experience a [1,4]-hydrogen shift, and in this case, the corresponding O-alkylimidates are formed as the final products. These ylides may also be stabilized by 1,3-dipolar electrocyclization with intermediate formation of an oxirane. Carbonyl ylides with an acyl group in the carbene moiety undergo an intramolecular 1,5-dipolar electrocyclization to produce 1,3-dioxole derivatives.

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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:06 Dec 2011 07:37
Last Modified:05 Apr 2016 15:07
Publisher:Wiley-Blackwell
ISSN:1099-0690
Funders:F. Hoffmann-La Roche AG, Basel
Publisher DOI:https://doi.org/10.1002/ejoc.200600396

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