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

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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 languageEnglish (US)
Pages (from-to)4005-4012
Number of pages8
JournalJournal of Organic Chemistry
Volume46
Issue number20
DOIs
StatePublished - Sep 1981
Externally publishedYes

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ASJC Scopus subject areas

  • Organic Chemistry

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