Structure and conformation of heterocycles. 13. conformational analysis of 2,3-DI(R)OXY-1,4-dioxanes: anomeric and gauche effects

Benzion Fuchs; Aviyakar Ellencweig; Ulrich Burkert

doi:10.1016/S0040-4020(01)88441-6

Structure and conformation of heterocycles. 13. conformational analysis of 2,3-DI(R)OXY-1,4-dioxanes: anomeric and gauche effects

Benzion Fuchs^*
, Aviyakar Ellencweig
, Ulrich Burkert

^*Corresponding author for this work

School of Chemistry

Tel Aviv University
University of Konstanz

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

25 Scopus citations

Abstract

A series of trans- and cis-2,3-di R)oxy-1,4-dIoxanes (R = Me,Ph, Ac) and some 2,5-disubstituted analogis were prepared and analysed by various NMR techniques. The trans isomers occur in more than 96% as diaxial conformers. Molecular mechanics calculations largely confirm these findings, which are interpreted -in terms of combined anomeric and gauche effects.

Original language	English
Pages (from-to)	2011-2021
Number of pages	11
Journal	Tetrahedron
Volume	40
Issue number	11
DOIs	https://doi.org/10.1016/S0040-4020(01)88441-6
State	Published - 1984

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title = "Structure and conformation of heterocycles. 13. conformational analysis of 2,3-DI(R)OXY-1,4-dioxanes: anomeric and gauche effects",

abstract = "A series of trans- and cis-2,3-di R)oxy-1,4-dIoxanes (R = Me,Ph, Ac) and some 2,5-disubstituted analogis were prepared and analysed by various NMR techniques. The trans isomers occur in more than 96\% as diaxial conformers. Molecular mechanics calculations largely confirm these findings, which are interpreted -in terms of combined anomeric and gauche effects.",

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AU - Fuchs, Benzion

AU - Ellencweig, Aviyakar

AU - Burkert, Ulrich

PY - 1984

Y1 - 1984

N2 - A series of trans- and cis-2,3-di R)oxy-1,4-dIoxanes (R = Me,Ph, Ac) and some 2,5-disubstituted analogis were prepared and analysed by various NMR techniques. The trans isomers occur in more than 96% as diaxial conformers. Molecular mechanics calculations largely confirm these findings, which are interpreted -in terms of combined anomeric and gauche effects.

AB - A series of trans- and cis-2,3-di R)oxy-1,4-dIoxanes (R = Me,Ph, Ac) and some 2,5-disubstituted analogis were prepared and analysed by various NMR techniques. The trans isomers occur in more than 96% as diaxial conformers. Molecular mechanics calculations largely confirm these findings, which are interpreted -in terms of combined anomeric and gauche effects.

UR - https://www.scopus.com/pages/publications/0008681986

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AN - SCOPUS:0008681986

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Structure and conformation of heterocycles. 13. conformational analysis of 2,3-DI(R)OXY-1,4-dioxanes: anomeric and gauche effects

Abstract

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