Conformational behaviour of medium-sized rings. Part 15.1 1,9,17- triaza[2.2.2]metacyclophane-2,10,18-trione derivatives

Farouk Eltayeb Elhadi, W. David Ollis*, J. Fraser Stoddart

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

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 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 languageEnglish (US)
Pages (from-to)1727-1732
Number of pages6
JournalJournal of the Chemical Society, Perkin Transactions 1
DOIs
StatePublished - 1982

ASJC Scopus subject areas

  • Chemistry(all)

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