Regio- and stereoselectivity of [2+3]cycloaddition of nitroethene to (Z)-N-aryl-C-phenylnitrones

[img]PDF - Authorized users only
Language: English
332Kb
Title:Regio- and stereoselectivity of [2+3]cycloaddition of nitroethene to (Z)-N-aryl-C-phenylnitrones
Creators:
Jasiński, Radomir
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 74, 9, pp. 1341-1349
Uncontrolled Keywords:Regioselectivity, Isoxazolidines, [2+3]Cycloadditions, DFT calculations, Stereoselectivity, Nitrones, Dipolar cycloadditions, Nitroethene

Abstract

The cycloaddition reactions of nitroethene to (<i>Z</i>)-<i>N</i>-aryl-<i>C</i>-phenylnitrones lead to mixtures of stereoisomeric <i>cis</i>- and <i>trans</i>-2-aryl-4-nitro-3-phenylisoxazolidines. Regioselectivity of these reactions is determined by the character of nucleophile–electrophile interactions, while stereoselectivity is determined by the steric factors and the character of secondary orbital interactions.

Title:Regio- and stereoselectivity of [2+3]cycloaddition of nitroethene to (Z)-N-aryl-C-phenylnitrones
Creators:
Jasiński, Radomir
Uncontrolled Keywords:Regioselectivity, Isoxazolidines, [2+3]Cycloadditions, DFT calculations, Stereoselectivity, Nitrones, Dipolar cycloadditions, Nitroethene
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:74
Number:9
Page Range:pp. 1341-1349
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc2009037UNSPECIFIED
ID Code:4770
Item Type:Article
Deposited On:17 Dec 2009 11:52
Last Modified:17 Dec 2009 10:52

Citation

Jasiński, Radomir (2009) Regio- and stereoselectivity of [2+3]cycloaddition of nitroethene to (Z)-N-aryl-C-phenylnitrones. Collection of Czechoslovak Chemical Communications, 74 (9). pp. 1341-1349. ISSN 0010-0765

Repository Staff Only: item control page