The Conformational Behaviour of 10‐Substituted Spiro[4.5]decanes

J. Jens Wolff; Gernot Frenking; Klaus Harms

doi:10.1002/cber.19911240322

The Conformational Behaviour of 10‐Substituted Spiro[4.5]decanes

J. Jens Wolff, Gernot Frenking, Klaus Harms

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18 Scopus citations

Abstract

The conformational behaviour of 10‐X‐substituted 1,4‐dioxa‐and 1,4,6‐trioxaspiro[4.5]decanes 1 – 4 has been studied by ¹³C‐, ¹⁹F‐ and ¹H‐NMR spectroscopy. Two X‐ray analyses (of 2a,e) are presented, and their implications to cleavage reactions of chiral acetals are discussed. Participation of twist boat forms in the conformeric equilibrium of at least 1c has been made plausible by observing ¹³C,¹⁹F‐NMR coupling constants. The ratios of axial to equatorial conformer in 1 – 4 have been calculated by molecular mechanics.

Original language	English
Pages (from-to)	551-561
Number of pages	11
Journal	Chemische Berichte
Volume	124
Issue number	3
DOIs	https://doi.org/10.1002/cber.19911240322
State	Published - 1991
Externally published	Yes

Keywords

Allylboration, transition state models
Calculations, MNDO and SYBYL
Conformational analysis
Ketals, chiral, cleavage by Lewis acids
Spiro[4.5]decanes

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10.1002/cber.19911240322

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title = "The Conformational Behaviour of 10‐Substituted Spiro[4.5]decanes",

abstract = "The conformational behaviour of 10‐X‐substituted 1,4‐dioxa‐and 1,4,6‐trioxaspiro[4.5]decanes 1 – 4 has been studied by 13C‐, 19F‐ and 1H‐NMR spectroscopy. Two X‐ray analyses (of 2a,e) are presented, and their implications to cleavage reactions of chiral acetals are discussed. Participation of twist boat forms in the conformeric equilibrium of at least 1c has been made plausible by observing 13C,19F‐NMR coupling constants. The ratios of axial to equatorial conformer in 1 – 4 have been calculated by molecular mechanics.",

keywords = "Allylboration, transition state models, Calculations, MNDO and SYBYL, Conformational analysis, Ketals, chiral, cleavage by Lewis acids, Spiro[4.5]decanes",

author = "{Jens Wolff}, J. and Gernot Frenking and Klaus Harms",

year = "1991",

doi = "10.1002/cber.19911240322",

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AU - Jens Wolff, J.

AU - Frenking, Gernot

AU - Harms, Klaus

PY - 1991

Y1 - 1991

N2 - The conformational behaviour of 10‐X‐substituted 1,4‐dioxa‐and 1,4,6‐trioxaspiro[4.5]decanes 1 – 4 has been studied by 13C‐, 19F‐ and 1H‐NMR spectroscopy. Two X‐ray analyses (of 2a,e) are presented, and their implications to cleavage reactions of chiral acetals are discussed. Participation of twist boat forms in the conformeric equilibrium of at least 1c has been made plausible by observing 13C,19F‐NMR coupling constants. The ratios of axial to equatorial conformer in 1 – 4 have been calculated by molecular mechanics.

AB - The conformational behaviour of 10‐X‐substituted 1,4‐dioxa‐and 1,4,6‐trioxaspiro[4.5]decanes 1 – 4 has been studied by 13C‐, 19F‐ and 1H‐NMR spectroscopy. Two X‐ray analyses (of 2a,e) are presented, and their implications to cleavage reactions of chiral acetals are discussed. Participation of twist boat forms in the conformeric equilibrium of at least 1c has been made plausible by observing 13C,19F‐NMR coupling constants. The ratios of axial to equatorial conformer in 1 – 4 have been calculated by molecular mechanics.

KW - Allylboration, transition state models

KW - Calculations, MNDO and SYBYL

KW - Conformational analysis

KW - Ketals, chiral, cleavage by Lewis acids

KW - Spiro[4.5]decanes

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JO - Chemische Berichte

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The Conformational Behaviour of 10‐Substituted Spiro[4.5]decanes

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