Journal of Organic Chemistry p. 4530 - 4536 (1981)
Update date:2022-08-05
Topics:
Mazzocchi, Paul H.
Ammon, Herman L.
Liu, Leslie
Colicelli, Elena
Ravi, Prasad
Burrows, Elizabeth
A series of diphenyl ethers linked to 2-azabicyclo<2.2.2>octan-3-ones and 2-azabicyclo<2.2.1>heptan-3-ones were synthesized as substrates for conformational analysis using the lanthanide shift reagent NMR technique.The materials were prepared by displacement of the exo-6-tosyloxy bicyclic lactam with the corresponding phenoxide which results in formation of the phenyl ether with retention of stereochemistry.This double-inversion process presumably involves anchimeric assistance by the lactam nitrogen.The synthesis and properties of a number of these systems are described.Complete 13C assignments for the series are presented.
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