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Rh(II)-Сatalyzed Reactions of Diazocarbonyl Compounds with Dicarboximides. / Nikolaev, Vs.V.; Heimgartner, H.; Linden, A.; Krylov, I.S.; Nikolaev, V.A.

In: European Journal of Organic Chemistry, No. 20, 2006, p. 4737-4746.

Research output: Contribution to journal › Article

Harvard

Nikolaev, VV, Heimgartner, H, Linden, A, Krylov, IS & Nikolaev, VA 2006, 'Rh(II)-Сatalyzed Reactions of Diazocarbonyl Compounds with Dicarboximides', European Journal of Organic Chemistry, no. 20, pp. 4737-4746. https://doi.org/DOI: 10.1002/ejoc.200600396

APA

Nikolaev, V. V., Heimgartner, H., Linden, A., Krylov, I. S., & Nikolaev, V. A. (2006). Rh(II)-Сatalyzed Reactions of Diazocarbonyl Compounds with Dicarboximides. European Journal of Organic Chemistry, (20), 4737-4746. https://doi.org/DOI: 10.1002/ejoc.200600396

Vancouver

Nikolaev VV, Heimgartner H, Linden A, Krylov IS, Nikolaev VA. Rh(II)-Сatalyzed Reactions of Diazocarbonyl Compounds with Dicarboximides. European Journal of Organic Chemistry. 2006;(20):4737-4746. https://doi.org/DOI: 10.1002/ejoc.200600396

Author

Nikolaev, Vs.V. ; Heimgartner, H. ; Linden, A. ; Krylov, I.S. ; Nikolaev, V.A. / Rh(II)-Сatalyzed Reactions of Diazocarbonyl Compounds with Dicarboximides. In: European Journal of Organic Chemistry. 2006 ; No. 20. pp. 4737-4746.

BibTeX

@article{7a1d618f0a704da0ae0f04f6e4ac7d11,
title = "Rh(II)-Сatalyzed Reactions of Diazocarbonyl Compounds with Dicarboximides",
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 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 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.",
keywords = "Diazo compounds, Imides, Rhodium–carbenoids, Carbonyl ylides, Insertion reactions, Imidates, Dipolar electrocyclization, Spiro compounds",
author = "Vs.V. Nikolaev and H. Heimgartner and A. Linden and I.S. Krylov and V.A. Nikolaev",
year = "2006",
doi = "DOI: 10.1002/ejoc.200600396",
language = "не определен",
pages = "4737--4746",
journal = "Liebigs Annalen der Chemie",
issn = "1434-193X",
publisher = "Wiley-Blackwell",
number = "20",

}

RIS

TY - JOUR

T1 - Rh(II)-Сatalyzed Reactions of Diazocarbonyl Compounds with Dicarboximides

AU - Nikolaev, Vs.V.

AU - Heimgartner, H.

AU - Linden, A.

AU - Krylov, I.S.

AU - Nikolaev, V.A.

PY - 2006

Y1 - 2006

N2 - 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 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 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.

AB - 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 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 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.

KW - Diazo compounds

KW - Imides

KW - Rhodium–carbenoids

KW - Carbonyl ylides

KW - Insertion reactions

KW - Imidates

KW - Dipolar electrocyclization

KW - Spiro compounds

U2 - DOI: 10.1002/ejoc.200600396

DO - DOI: 10.1002/ejoc.200600396

M3 - статья

SP - 4737

EP - 4746

JO - Liebigs Annalen der Chemie

JF - Liebigs Annalen der Chemie

SN - 1434-193X

IS - 20

ER -

ID: 5201824