Nitrogen-15 NMR spectra of tertiary amines with the 7-azanorbornene framework

Quin, Louis D.; Caster, Kenneth C.; Marsi, B. G.; Miller, Joseph A.

doi:10.1021/jo00369a038

Cited by 9 publications

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“…[148][149][150][151][152] Restricted nitrogen inversion in 7-azabicyclo[2.2.1]-hepta-2,5-diene derivatives has also been studied. [153][154][155][156][157][158][159][160][161] A similar bicyclic effect has been found to exist.…”

Section: Physical and Spectroscopic Characteristicssupporting

confidence: 65%

“…The 7-azabicyclo[2.2.1]heptane derivatives have been shown to posses an especially high nitrogen inversion barrier which is on the order of ∼3.5 kcal/mol relative to an α-unbranched monocyclic compound of the same pyramidal geometry at nitrogen − Restricted nitrogen inversion in 7-azabicyclo[2.2.1]hepta-2,5-diene derivatives has also been studied. − A similar bicyclic effect has been found to exist. …”

Section: Physical and Spectroscopic Characteristicsmentioning

confidence: 96%

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Chemistry of 7-Azabicyclo[2.2.1]hepta-2,5-dienes, 7-Azabicyclo[2.2.1]hept-2-enes, and 7-Azabicyclo[2.2.1]heptanes

1996

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ContentsI. Introduction 1179 II. Preparation of 7-Azabicyclo[2.2.1]hepta-2,5-dienes and 7-Azabicyclo[2.2.1]hept-2-enes by the [4+2] Cycloaddition Reaction 1179 A. Lewis Acid Catalyzed Reactions 1181 B. High-Pressure and Ultrasound Reactions 1182 C. Reactions with Acetylene Equivalents 1183 D. Miscellaneous Reactions 1183 III. Chemistry of the 7-Azabicyclo[2.2.1]hepta-2,5-dienes and 7-Azabicyclo[2.2.1]hept-2-enes 1184 A. Synthesis of Substituted Pyrroles 1184 B. Synthesis of Substituted Arene Derivatives 1185 C. Synthesis of the Organometallic Complexes 1187 IV. Synthetic Approaches to the 7-Azabicyclo[2.2.1]heptanes 1187 A. Intramolecular Cyclization of Cyclohexylamine Derivatives 1187 B. Reduction of 7-Azabicyclo[2.2.1]hepta-2,5-dienes and 7-Azabicyclo[2.2.1]hept-2-enes 1188 C. [3+2] Cycloaddition Reactions 1189 D. Intramolecular Cyclization of Substituted Proline Derivatives 1189 E. Miscellaneous Reactions 1190 V. Properties of 7-Azabicyclo[2.2.1]heptane Derivatives 1190 A. 7-Azabicyclo[2.2.1]heptane and 7-Azabicyclo-[2.2.1]heptene Derivatives as Potential Chemotherapeutic Drugs 1190

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