In-line proximity effects in extended 7-azanorbornanes. 2. a major reduction of N-inversion barriers in symmetrically flanked systems

John R. Malpass, Douglas N. Butler, Martin R. Johnston, Malcom L.A. Hammond, Ronald N. Warrener

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

Dynamic Dynamic (figure presented) oscillation angle decreases as size of sentinel X increases Through-space compression effects from a pair of flanking (sentinel) groups X are shown to cause a flattening of the bridging nitrogen in symmetrically fused 7-azanorbornanes which is evaluated by a substantial reduction of the nitrogen inversion barrier as measured by low-temperature 1H NMR spectroscopy. This effect is attributed to destabilization of the ground state of the amine.

Original languageEnglish
Pages (from-to)725-728
Number of pages4
JournalOrganic Letters
Volume2
Issue number6
DOIs
Publication statusPublished - 3 Mar 2000
Externally publishedYes

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