TY - JOUR
T1 - Conformational behaviour of medium-sized rings. Part 15.1 1,9,17- triaza[2.2.2]metacyclophane-2,10,18-trione derivatives
AU - Elhadi, Farouk Eltayeb
AU - Ollis, W. David
AU - Stoddart, J. Fraser
PY - 1982
Y1 - 1982
N2 - 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.
AB - 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.
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U2 - 10.1039/P19820001727
DO - 10.1039/P19820001727
M3 - Article
AN - SCOPUS:0006372101
SN - 1470-4358
SP - 1727
EP - 1732
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
ER -