Conformational behaviour of medium-sized rings. Part 15. 1,9,17-Triaza[2.2.2]metacyclophane-2,10,1 8-trione derivatives
- 1 January 1982
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 1727-1732
- https://doi.org/10.1039/p19820001727
Abstract
The stepwise synthesis of 1,9-dimethyl-1,9,17-triaza[2.2.2]metacyclophane-2,10,18-trione (1) from methyl m-aminobenzoate and m-nitrobenzoyl chloride is reported. The temperature dependences (i) of the 1H-decoupled 13C n.m.r. spectrum of the 1, 9,17-trimethyl derivative (2) and (ii) of the 1H n.m.r. spectrum of the 1,9-dimethyl-17-benzyl derivative (3) are interpreted in terms of equilibration between diastereoisomeric crown and saddle conformations in solution. The 1,9-dimethyl derivative (1) is believed to exist predominantly in the saddle conformation in solution.Keywords
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