Stereochemical study on the cycloaddition of a cyclic nitrone to 5‐methyl‐2(5H)‐furanone

Marta Figueredo; Josep Font; Pedro De March

doi:10.1002/cber.19891220916

Stereochemical study on the cycloaddition of a cyclic nitrone to 5‐methyl‐2(5H)‐furanone

Marta Figueredo, Josep Font, Pedro De March

Department of Chemistry

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

23 Citations (Scopus)

Abstract

The 1,3‐Dipolar cycloaddition of 3,4,5,6‐tetrahydropyridine 1‐oxide (1) to 5‐methyl‐2(5H)‐furanone (2) yields adducts 3, 4, and 5, whose stereochemistry has been established by a detailed study of their low‐temperature 1H‐NMR spectra. The major adduct, 4, arises from an exo transition state and an anti approach, indicating the dominance of steric factors over secondary orbital interactions. Copyright © 1989 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim

Original language	English
Pages (from-to)	1701-1704
Journal	Chemische Berichte
Volume	122
Issue number	9
DOIs	https://doi.org/10.1002/cber.19891220916
Publication status	Published - 1 Jan 1989

Keywords

1,3‐Dipolar cycloaddition
3,4,5,6‐Tetrahydropyridine 1‐oxide
5‐Methyl‐2(5H)‐furanone
Methyl sorbate

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10.1002/cber.19891220916

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title = "Stereochemical study on the cycloaddition of a cyclic nitrone to 5‐methyl‐2(5H)‐furanone",

abstract = "The 1,3‐Dipolar cycloaddition of 3,4,5,6‐tetrahydropyridine 1‐oxide (1) to 5‐methyl‐2(5H)‐furanone (2) yields adducts 3, 4, and 5, whose stereochemistry has been established by a detailed study of their low‐temperature 1H‐NMR spectra. The major adduct, 4, arises from an exo transition state and an anti approach, indicating the dominance of steric factors over secondary orbital interactions. Copyright {\textcopyright} 1989 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim",

keywords = "1,3‐Dipolar cycloaddition, 3,4,5,6‐Tetrahydropyridine 1‐oxide, 5‐Methyl‐2(5H)‐furanone, Methyl sorbate",

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year = "1989",

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T1 - Stereochemical study on the cycloaddition of a cyclic nitrone to 5‐methyl‐2(5H)‐furanone

AU - Figueredo, Marta

AU - Font, Josep

AU - De March, Pedro

PY - 1989/1/1

Y1 - 1989/1/1

N2 - The 1,3‐Dipolar cycloaddition of 3,4,5,6‐tetrahydropyridine 1‐oxide (1) to 5‐methyl‐2(5H)‐furanone (2) yields adducts 3, 4, and 5, whose stereochemistry has been established by a detailed study of their low‐temperature 1H‐NMR spectra. The major adduct, 4, arises from an exo transition state and an anti approach, indicating the dominance of steric factors over secondary orbital interactions. Copyright © 1989 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim

AB - The 1,3‐Dipolar cycloaddition of 3,4,5,6‐tetrahydropyridine 1‐oxide (1) to 5‐methyl‐2(5H)‐furanone (2) yields adducts 3, 4, and 5, whose stereochemistry has been established by a detailed study of their low‐temperature 1H‐NMR spectra. The major adduct, 4, arises from an exo transition state and an anti approach, indicating the dominance of steric factors over secondary orbital interactions. Copyright © 1989 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim

KW - 1,3‐Dipolar cycloaddition

KW - 3,4,5,6‐Tetrahydropyridine 1‐oxide

KW - 5‐Methyl‐2(5H)‐furanone

KW - Methyl sorbate

U2 - 10.1002/cber.19891220916

DO - 10.1002/cber.19891220916

M3 - Article

VL - 122

SP - 1701

EP - 1704

JO - Chemische Berichte

JF - Chemische Berichte

SN - 0009-2940

IS - 9

ER -

Stereochemical study on the cycloaddition of a cyclic nitrone to 5‐methyl‐2(5H)‐furanone

Abstract

Keywords

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