Issue 0, 1982

Conformational behaviour of medium-sized rings. Part 15. 1,9,17-Triaza[2.2.2]metacyclophane-2,10,1 8-trione derivatives

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.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1982, 1727-1732

Conformational behaviour of medium-sized rings. Part 15. 1,9,17-Triaza[2.2.2]metacyclophane-2,10,1 8-trione derivatives

F. E. Elhadi, W. D. Ollis and J. F. Stoddart, J. Chem. Soc., Perkin Trans. 1, 1982, 1727 DOI: 10.1039/P19820001727

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