The 1,3-dipolar cycloaddition of cyclic nitrones with 1,2-disubstituted alkenes

Sk Asrof Ali; Javaid H. Khan; Mohammed I.M. Wazeer; Herman P. Perzanowski

doi:10.1016/S0040-4020(01)89124-9

The 1,3-dipolar cycloaddition of cyclic nitrones with 1,2-disubstituted alkenes

Sk Asrof Ali^*
, Javaid H. Khan
, Mohammed I.M. Wazeer
, Herman P. Perzanowski

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

31 Scopus citations

Abstract

A comparative study of the stereochemical behaviour of the 1,3-dipolar cycloaddition of a series of 1,2-disubstituted alkenes with 1-pyrroline 1-oxide (1) and 2,3,4,5-tetrahydropyridine 1-oxide (2) has been carried out. Both the nitrones exhibit very similar stereochemical properties. Rate constants for the cycloaddition of these nitrones to several disubstituted alkenes have been determinded at 36°C by ¹H n.m.r. spectroscopy. It is found that the nitrone 1 reacts slower than 2 due to the presence of bond eclipsing strain in the transition state involving 1.

Original language	English
Pages (from-to)	5979-5986
Number of pages	8
Journal	Tetrahedron
Volume	45
Issue number	18
DOIs	https://doi.org/10.1016/S0040-4020(01)89124-9
State	Published - 1989

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "The 1,3-dipolar cycloaddition of cyclic nitrones with 1,2-disubstituted alkenes",

abstract = "A comparative study of the stereochemical behaviour of the 1,3-dipolar cycloaddition of a series of 1,2-disubstituted alkenes with 1-pyrroline 1-oxide (1) and 2,3,4,5-tetrahydropyridine 1-oxide (2) has been carried out. Both the nitrones exhibit very similar stereochemical properties. Rate constants for the cycloaddition of these nitrones to several disubstituted alkenes have been determinded at 36°C by 1H n.m.r. spectroscopy. It is found that the nitrone 1 reacts slower than 2 due to the presence of bond eclipsing strain in the transition state involving 1.",

author = "Ali, \{Sk Asrof\} and Khan, \{Javaid H.\} and Wazeer, \{Mohammed I.M.\} and Perzanowski, \{Herman P.\}",

year = "1989",

doi = "10.1016/S0040-4020(01)89124-9",

language = "English",

volume = "45",

pages = "5979--5986",

journal = "Tetrahedron",

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T1 - The 1,3-dipolar cycloaddition of cyclic nitrones with 1,2-disubstituted alkenes

AU - Ali, Sk Asrof

AU - Khan, Javaid H.

AU - Wazeer, Mohammed I.M.

AU - Perzanowski, Herman P.

PY - 1989

Y1 - 1989

N2 - A comparative study of the stereochemical behaviour of the 1,3-dipolar cycloaddition of a series of 1,2-disubstituted alkenes with 1-pyrroline 1-oxide (1) and 2,3,4,5-tetrahydropyridine 1-oxide (2) has been carried out. Both the nitrones exhibit very similar stereochemical properties. Rate constants for the cycloaddition of these nitrones to several disubstituted alkenes have been determinded at 36°C by 1H n.m.r. spectroscopy. It is found that the nitrone 1 reacts slower than 2 due to the presence of bond eclipsing strain in the transition state involving 1.

AB - A comparative study of the stereochemical behaviour of the 1,3-dipolar cycloaddition of a series of 1,2-disubstituted alkenes with 1-pyrroline 1-oxide (1) and 2,3,4,5-tetrahydropyridine 1-oxide (2) has been carried out. Both the nitrones exhibit very similar stereochemical properties. Rate constants for the cycloaddition of these nitrones to several disubstituted alkenes have been determinded at 36°C by 1H n.m.r. spectroscopy. It is found that the nitrone 1 reacts slower than 2 due to the presence of bond eclipsing strain in the transition state involving 1.

UR - https://www.scopus.com/pages/publications/0000567563

U2 - 10.1016/S0040-4020(01)89124-9

DO - 10.1016/S0040-4020(01)89124-9

M3 - Article

AN - SCOPUS:0000567563

SN - 0040-4020

VL - 45

SP - 5979

EP - 5986

JO - Tetrahedron

JF - Tetrahedron

IS - 18

ER -

The 1,3-dipolar cycloaddition of cyclic nitrones with 1,2-disubstituted alkenes

Abstract

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