Journal of the Chemical Society. Perkin transactions I p. 1727 - 1732 (1982)
Update date:2022-07-30
Topics:
Elhadi, Farouk Eltayeb
Ollis, W. David
Stoddart, J. Fraser
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.
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