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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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

Bibliographical note

Funding Information:
REFERENCES ’ Previous Paper: P. S. Portoghese. A. A. Mikhail and H. J. Kupferberg, J. Med. Gem. 11,219 (1968) 2 This investigation was supported by Public Health Service Grant GM 09402 ’ Presented in part at the 154rh Narionul Meeting oft he American Chemical Society. Abstract P-16. Chicago, lllino~ September (1967) 4 P. S. Portoghese and A. A. Mikhail, 1. Org. Gem. 31.1059 (1966) ’ A. A. Patchett and B. Witkop, J. Am. C/tern. Sot. 79,185 (1957) ’ M. Karplus, J. C&m. Phys. 30.11 (1959) ’ F. A. L. Anet, Canad. J. Gem. 39,789 (1961). and refs cited s A. M. Mikhail. Ph.D. Dissertation University of Minnesota (1966) e H. S. Gutowsky and C. H. Helm, J. Chem. Phys. 25. 1228 (1956) to F. A. Bovey, Nuclear Magnetic Resonance Spectroscopy p. 190. Academic Press, New York (1969)

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