1,3-DIPOLAR CYCLOADDITION OF PHENYL AZIDE TO NORBORNENE IN AQUEOUS-SOLUTIONS

J.W Wijnen; R.A. Steiner; J.B.F.N. Engberts

doi:10.1016/0040-4039(95)00987-N

1,3-DIPOLAR CYCLOADDITION OF PHENYL AZIDE TO NORBORNENE IN AQUEOUS-SOLUTIONS

J.W Wijnen, R.A. Steiner, J.B.F.N. Engberts

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Abstract

Second-order rate constants for the cycloaddition of phenyl azide to norbornene were determined in aqueous solutions. In organic solvents this reaction shows a very small solvent effect. In highly aqueous media, however, remarkable accelerations are observed. The solvent dependence of the rate constants on solvent composition in mixed aqueous solutions resembles those observed for Diels-Alder reactions, most likely because both types of cycloadditions are mechanistically related.

Original language	English
Pages (from-to)	5389-5392
Number of pages	4
Journal	Tetrahedron Letters
Volume	36
Issue number	30
DOIs	https://doi.org/10.1016/0040-4039(95)00987-N
Publication status	Published - 24-Jul-1995

Keywords

DIELS-ALDER REACTIONS
CARBON
WATER

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title = "1,3-DIPOLAR CYCLOADDITION OF PHENYL AZIDE TO NORBORNENE IN AQUEOUS-SOLUTIONS",

abstract = "Second-order rate constants for the cycloaddition of phenyl azide to norbornene were determined in aqueous solutions. In organic solvents this reaction shows a very small solvent effect. In highly aqueous media, however, remarkable accelerations are observed. The solvent dependence of the rate constants on solvent composition in mixed aqueous solutions resembles those observed for Diels-Alder reactions, most likely because both types of cycloadditions are mechanistically related.",

keywords = "DIELS-ALDER REACTIONS, CARBON, WATER",

author = "J.W Wijnen and R.A. Steiner and J.B.F.N. Engberts",

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AU - Wijnen, J.W

AU - Steiner, R.A.

AU - Engberts, J.B.F.N.

N1 - Journal UL 24 K579 ETRAHEDRON LETT

PY - 1995/7/24

Y1 - 1995/7/24

N2 - Second-order rate constants for the cycloaddition of phenyl azide to norbornene were determined in aqueous solutions. In organic solvents this reaction shows a very small solvent effect. In highly aqueous media, however, remarkable accelerations are observed. The solvent dependence of the rate constants on solvent composition in mixed aqueous solutions resembles those observed for Diels-Alder reactions, most likely because both types of cycloadditions are mechanistically related.

AB - Second-order rate constants for the cycloaddition of phenyl azide to norbornene were determined in aqueous solutions. In organic solvents this reaction shows a very small solvent effect. In highly aqueous media, however, remarkable accelerations are observed. The solvent dependence of the rate constants on solvent composition in mixed aqueous solutions resembles those observed for Diels-Alder reactions, most likely because both types of cycloadditions are mechanistically related.

KW - DIELS-ALDER REACTIONS

KW - CARBON

KW - WATER

U2 - 10.1016/0040-4039(95)00987-N

DO - 10.1016/0040-4039(95)00987-N

M3 - Article

VL - 36

SP - 5389

EP - 5392

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 30

ER -

1,3-DIPOLAR CYCLOADDITION OF PHENYL AZIDE TO NORBORNENE IN AQUEOUS-SOLUTIONS

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