Tetrahedron

Bicyclic bases: Synthesis and nuclear magnetic resonance investigation of some chiral 2-oxa-5-azabicyclo [2.2. 1] Heptane derivatives

PS Portoghese, JG Turcotte

文献索引：Portoghese,P.S.; Turcotte,J.G. Tetrahedron, 1971 , vol. 27, p. 961 - 967

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被引用次数: 28

摘要

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 N CO rotation in 7 is≈ 2 Kcal/mole higher than for 8. Possible explanations for the difference in ΔG‡ are discussed.