On Structural Determination of C-7-Substituted 6,8-Dioxabicyclo[3.2.1]octanes. A Reevaluation

Bradford P. Mundy; Gary W. Dirks; Raima M. Barter; Arnold C. Craig; Kenneth B. Bipkowitz; John Carter

doi:10.1021/jo00333a014

On Structural Determination of C-7-Substituted 6,8-Dioxabicyclo[3.2.1]octanes. A Reevaluation

Bradford P. Mundy, Gary W. Dirks, Raima M. Barter, Arnold C. Craig, Kenneth B. Bipkowitz, John Carter

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

16 Scopus citations

Abstract

The use of mass spectral and lanthanide shift reagent NMR data for structural elucidation in the 6,8-dioxabicyclo[3.2.1]octane series is examined. Sufficient irregularities associated with 7-substituted members of this series are found to prompt a cautionary response to their unconditional use in determining structures of these bicyclic ketals. A molecular mechanics calculational analysis of various members of the series examines how substituents affect the conformation of these ketals. CNDO/2 calculations to evaluate the Lewis basicity of the two ketal oxygens lead to the conclusion that any preferential coordination will most likely find its origins in steric rather than electronic effects.

Original language	English (US)
Pages (from-to)	4005-4012
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	46
Issue number	20
DOIs	https://doi.org/10.1021/jo00333a014
State	Published - Sep 1981
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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title = "On Structural Determination of C-7-Substituted 6,8-Dioxabicyclo[3.2.1]octanes. A Reevaluation",

abstract = "The use of mass spectral and lanthanide shift reagent NMR data for structural elucidation in the 6,8-dioxabicyclo[3.2.1]octane series is examined. Sufficient irregularities associated with 7-substituted members of this series are found to prompt a cautionary response to their unconditional use in determining structures of these bicyclic ketals. A molecular mechanics calculational analysis of various members of the series examines how substituents affect the conformation of these ketals. CNDO/2 calculations to evaluate the Lewis basicity of the two ketal oxygens lead to the conclusion that any preferential coordination will most likely find its origins in steric rather than electronic effects.",

author = "Mundy, {Bradford P.} and Dirks, {Gary W.} and Barter, {Raima M.} and Craig, {Arnold C.} and Bipkowitz, {Kenneth B.} and John Carter",

year = "1981",

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language = "English (US)",

volume = "46",

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T1 - On Structural Determination of C-7-Substituted 6,8-Dioxabicyclo[3.2.1]octanes. A Reevaluation

AU - Mundy, Bradford P.

AU - Dirks, Gary W.

AU - Barter, Raima M.

AU - Craig, Arnold C.

AU - Bipkowitz, Kenneth B.

AU - Carter, John

PY - 1981/9

Y1 - 1981/9

N2 - The use of mass spectral and lanthanide shift reagent NMR data for structural elucidation in the 6,8-dioxabicyclo[3.2.1]octane series is examined. Sufficient irregularities associated with 7-substituted members of this series are found to prompt a cautionary response to their unconditional use in determining structures of these bicyclic ketals. A molecular mechanics calculational analysis of various members of the series examines how substituents affect the conformation of these ketals. CNDO/2 calculations to evaluate the Lewis basicity of the two ketal oxygens lead to the conclusion that any preferential coordination will most likely find its origins in steric rather than electronic effects.

AB - The use of mass spectral and lanthanide shift reagent NMR data for structural elucidation in the 6,8-dioxabicyclo[3.2.1]octane series is examined. Sufficient irregularities associated with 7-substituted members of this series are found to prompt a cautionary response to their unconditional use in determining structures of these bicyclic ketals. A molecular mechanics calculational analysis of various members of the series examines how substituents affect the conformation of these ketals. CNDO/2 calculations to evaluate the Lewis basicity of the two ketal oxygens lead to the conclusion that any preferential coordination will most likely find its origins in steric rather than electronic effects.

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On Structural Determination of C-7-Substituted 6,8-Dioxabicyclo[3.2.1]octanes. A Reevaluation

Abstract

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