Bicyclic bases. Synthesis and nuclear magnetic resonance investigation of some chiral 2-oxa-5-azabicyclo[2.2.1]Heptane derivatives

P. S. Portoghese, J. G. Turcotte

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20 Scopus citations

Abstract

The N-benzoyl derivatives of 2-oxa-5-azabicyclo[2.2.1]heptane (7) and of 2-oxa-5-azabicyclo [2.2.1]heptane-3-one (8) have been prepared from hydroxy-L-proline. The NMR spectra of these compounds have been analyzed with the aid of variable temperature studies. It was found that ΔG for NCO rotation in 7 is ≈ 2 Kcal/mole higher than for 8. Possible explanations for the difference in ΔG are discussed.

Original languageEnglish (US)
Pages (from-to)961-967
Number of pages7
JournalTetrahedron
Volume27
Issue number5
DOIs
StatePublished - 1971

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