, volume 45 , issue 31 , pages 6003-6006

Reactions of 2H-azirines with carbenoids from diazo esters: Transformations of novel azirinium ylides

Alexander F Khlebnikov ¹

Amer A Amer ¹

Mikhail S. Novikov ¹

Hide authors affiliations Show authors affiliations: 1 affiliation

Department of Chemistry, St. Petersburg State University, Universitetskii pr. 26, 198504 St. Petersburg,Petrodvorets,Russia |

Publication type: Journal Article

Publication date: 2004-07-21

Elsevier

Tetrahedron Letters

scimago Q3

wos Q3

SJR: 0.334

CiteScore: 3.2

Impact factor: 1.5

ISSN: 00404039, 18733581

DOI: 10.1016/j.tetlet.2004.06.038

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Organic Chemistry

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Abstract

Thermocatalytic decomposition of diazo esters in the presence of 3-aryl-2H-azirines gives rise to azirinium ylides. The latter preferentially transform via isomerization into 2-azabuta-1,3-diene derivatives or, with excess diazo compound, via reaction with the Rh-carbenoid to form 3,4-dihydro-2H-pyrrole derivatives. In contrast, ylides generated from 2-monosubstituted or 2,2-disubstituted 3-phenyl-2H-azirines transform exclusively via isomerization into the corresponding 2-azabuta-1,3-dienes in high yields.

Found

17 citations

Novikov Mikhail

DSc in Chemistry, associate professor

216 publications, 4 151 citations, 54 reviews

h-index: 33

Saint Petersburg State University

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Khlebnikov A. F., Amer A. A., Novikov M. S. Reactions of 2H-azirines with carbenoids from diazo esters: Transformations of novel azirinium ylides // Tetrahedron Letters. 2004. Vol. 45. No. 31. pp. 6003-6006.

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RIS |

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TY - JOUR

DO - 10.1016/j.tetlet.2004.06.038

UR - https://doi.org/10.1016/j.tetlet.2004.06.038

TI - Reactions of 2H-azirines with carbenoids from diazo esters: Transformations of novel azirinium ylides

T2 - Tetrahedron Letters

AU - Khlebnikov, Alexander F

AU - Amer, Amer A

AU - Novikov, Mikhail S.

PY - 2004

DA - 2004/07/21

PB - Elsevier

SP - 6003-6006

IS - 31

VL - 45

SN - 0040-4039

SN - 1873-3581

ER -

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@article{2004_Amer,

author = {Alexander F Khlebnikov and Amer A Amer and Mikhail S. Novikov},

title = {Reactions of 2H-azirines with carbenoids from diazo esters: Transformations of novel azirinium ylides},

journal = {Tetrahedron Letters},

year = {2004},

volume = {45},

publisher = {Elsevier},

month = {jul},

url = {https://doi.org/10.1016/j.tetlet.2004.06.038},

number = {31},

pages = {6003--6006},

doi = {10.1016/j.tetlet.2004.06.038}

}

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Amer, Amer A., et al. “Reactions of 2H-azirines with carbenoids from diazo esters: Transformations of novel azirinium ylides.” Tetrahedron Letters, vol. 45, no. 31, Jul. 2004, pp. 6003-6006. https://doi.org/10.1016/j.tetlet.2004.06.038.