Standard

Thermally induced tandem cycloaddition of 2-alkyl-3-phenylcyclopropenones to 6-aryl-1,5-diazabicyclo[3.1.0]hexanes. / Molchanov, A. P.; Sipkin, D. I.; Koptelov, Yu B.; Kostikov, R. R.

в: Russian Journal of Organic Chemistry, Том 41, № 4, 04.2005, стр. 567-574.

Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование

Harvard

Molchanov, AP, Sipkin, DI, Koptelov, YB & Kostikov, RR 2005, 'Thermally induced tandem cycloaddition of 2-alkyl-3-phenylcyclopropenones to 6-aryl-1,5-diazabicyclo[3.1.0]hexanes', Russian Journal of Organic Chemistry, Том. 41, № 4, стр. 567-574. https://doi.org/10.1007/s11178-005-0205-z

APA

Molchanov, A. P., Sipkin, D. I., Koptelov, Y. B., & Kostikov, R. R. (2005). Thermally induced tandem cycloaddition of 2-alkyl-3-phenylcyclopropenones to 6-aryl-1,5-diazabicyclo[3.1.0]hexanes. Russian Journal of Organic Chemistry, 41(4), 567-574. https://doi.org/10.1007/s11178-005-0205-z

Vancouver

Molchanov AP, Sipkin DI, Koptelov YB, Kostikov RR. Thermally induced tandem cycloaddition of 2-alkyl-3-phenylcyclopropenones to 6-aryl-1,5-diazabicyclo[3.1.0]hexanes. Russian Journal of Organic Chemistry. 2005 Апр.;41(4):567-574. https://doi.org/10.1007/s11178-005-0205-z

Author

Molchanov, A. P. ; Sipkin, D. I. ; Koptelov, Yu B. ; Kostikov, R. R. / Thermally induced tandem cycloaddition of 2-alkyl-3-phenylcyclopropenones to 6-aryl-1,5-diazabicyclo[3.1.0]hexanes. в: Russian Journal of Organic Chemistry. 2005 ; Том 41, № 4. стр. 567-574.

BibTeX

@article{183d7a57c1944af8ade771c01a70e471,
title = "Thermally induced tandem cycloaddition of 2-alkyl-3-phenylcyclopropenones to 6-aryl-1,5-diazabicyclo[3.1.0]hexanes",
abstract = "Thermolysis of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes in the presence of 2-alkyl-3-phenylcyclopropenones gives fused polycyclic systems of the 4a,7b-diazacyclopenta[cd]inden-7-one series as a result of addition of two cyclopropenone molecules and extrusion of CO molecule. The first step of the process is characterized by 100% regioselectivity, leading to the adduct with vicinal arrangement of the aryl groups, while the regioselectivity of the second step is likely to be determined by spatial interactions between substituents in the cyclopropenone molecule and trimethylene bridge of the diazabicyclohexane. Steric hindrances in the second step could eliminate formation of stable products.",
author = "Molchanov, {A. P.} and Sipkin, {D. I.} and Koptelov, {Yu B.} and Kostikov, {R. R.}",
note = "Funding Information: This study was performed under financial support by the Russian Foundation for Basic Research (project no. 04-03-32898). Copyright: Copyright 2008 Elsevier B.V., All rights reserved.",
year = "2005",
month = apr,
doi = "10.1007/s11178-005-0205-z",
language = "English",
volume = "41",
pages = "567--574",
journal = "Russian Journal of Organic Chemistry",
issn = "1070-4280",
publisher = "МАИК {"}Наука/Интерпериодика{"}",
number = "4",

}

RIS

TY - JOUR

T1 - Thermally induced tandem cycloaddition of 2-alkyl-3-phenylcyclopropenones to 6-aryl-1,5-diazabicyclo[3.1.0]hexanes

AU - Molchanov, A. P.

AU - Sipkin, D. I.

AU - Koptelov, Yu B.

AU - Kostikov, R. R.

N1 - Funding Information: This study was performed under financial support by the Russian Foundation for Basic Research (project no. 04-03-32898). Copyright: Copyright 2008 Elsevier B.V., All rights reserved.

PY - 2005/4

Y1 - 2005/4

N2 - Thermolysis of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes in the presence of 2-alkyl-3-phenylcyclopropenones gives fused polycyclic systems of the 4a,7b-diazacyclopenta[cd]inden-7-one series as a result of addition of two cyclopropenone molecules and extrusion of CO molecule. The first step of the process is characterized by 100% regioselectivity, leading to the adduct with vicinal arrangement of the aryl groups, while the regioselectivity of the second step is likely to be determined by spatial interactions between substituents in the cyclopropenone molecule and trimethylene bridge of the diazabicyclohexane. Steric hindrances in the second step could eliminate formation of stable products.

AB - Thermolysis of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes in the presence of 2-alkyl-3-phenylcyclopropenones gives fused polycyclic systems of the 4a,7b-diazacyclopenta[cd]inden-7-one series as a result of addition of two cyclopropenone molecules and extrusion of CO molecule. The first step of the process is characterized by 100% regioselectivity, leading to the adduct with vicinal arrangement of the aryl groups, while the regioselectivity of the second step is likely to be determined by spatial interactions between substituents in the cyclopropenone molecule and trimethylene bridge of the diazabicyclohexane. Steric hindrances in the second step could eliminate formation of stable products.

UR - http://www.scopus.com/inward/record.url?scp=21544473846&partnerID=8YFLogxK

U2 - 10.1007/s11178-005-0205-z

DO - 10.1007/s11178-005-0205-z

M3 - Article

VL - 41

SP - 567

EP - 574

JO - Russian Journal of Organic Chemistry

JF - Russian Journal of Organic Chemistry

SN - 1070-4280

IS - 4

ER -

ID: 5144212