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 the1H-decoupledl3C n.m.r. spectrum of the 1,9,17-trimethyl derivative (2) and (ii) of the1H 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.
|Original language||English (US)|
|Number of pages||6|
|Journal||Journal of the Chemical Society, Perkin Transactions 1|
|State||Published - 1982|
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