Synthesis and conformational behaviour of 1,9,17-triaza[2.2.2]metacyclophane-2, 10, 18-trione derivatives

Farouk Eltayeb Elhadi; W. David Ollis; J. Fraser Stoddart; David J. Williams; Kwamena A. Woode

doi:10.1016/S0040-4039(00)93692-X

Synthesis and conformational behaviour of 1,9,17-triaza[2.2.2]metacyclophane-2, 10, 18-trione derivatives

Farouk Eltayeb Elhadi^*, W. David Ollis, J. Fraser Stoddart, David J. Williams, Kwamena A. Woode

^*Corresponding author for this work

Chemistry

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Abstract

The 1,9,17-triaza[2.2.2]metacyclophane-2, 10, 18-trione derivatives (1) - (3) have been synthesised. X-Ray crystallography shows that the 1,9,17-trimethyl derivative (3) adopts a Crown conformation (11) in the solid state. Dynamic n.m.r. spectroscopy indicates that both the 1,9-dimethyl-17-benzyl- (2) and 1,9,17-trimethyl- (3) derivatives exist as interconverting mixtures of Crown (11) and Saddle (12) conformations with the former predominating at equilibrium in solution.

Original language	English (US)
Pages (from-to)	4215-4218
Number of pages	4
Journal	Tetrahedron Letters
Volume	21
Issue number	43
DOIs	https://doi.org/10.1016/S0040-4039(00)93692-X
State	Published - 1980

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Synthesis and conformational behaviour of 1,9,17-triaza[2.2.2]metacyclophane-2, 10, 18-trione derivatives",

abstract = "The 1,9,17-triaza[2.2.2]metacyclophane-2, 10, 18-trione derivatives (1) - (3) have been synthesised. X-Ray crystallography shows that the 1,9,17-trimethyl derivative (3) adopts a Crown conformation (11) in the solid state. Dynamic n.m.r. spectroscopy indicates that both the 1,9-dimethyl-17-benzyl- (2) and 1,9,17-trimethyl- (3) derivatives exist as interconverting mixtures of Crown (11) and Saddle (12) conformations with the former predominating at equilibrium in solution.",

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T1 - Synthesis and conformational behaviour of 1,9,17-triaza[2.2.2]metacyclophane-2, 10, 18-trione derivatives

AU - Elhadi, Farouk Eltayeb

AU - David Ollis, W.

AU - Fraser Stoddart, J.

AU - Williams, David J.

AU - Woode, Kwamena A.

PY - 1980

Y1 - 1980

N2 - The 1,9,17-triaza[2.2.2]metacyclophane-2, 10, 18-trione derivatives (1) - (3) have been synthesised. X-Ray crystallography shows that the 1,9,17-trimethyl derivative (3) adopts a Crown conformation (11) in the solid state. Dynamic n.m.r. spectroscopy indicates that both the 1,9-dimethyl-17-benzyl- (2) and 1,9,17-trimethyl- (3) derivatives exist as interconverting mixtures of Crown (11) and Saddle (12) conformations with the former predominating at equilibrium in solution.

AB - The 1,9,17-triaza[2.2.2]metacyclophane-2, 10, 18-trione derivatives (1) - (3) have been synthesised. X-Ray crystallography shows that the 1,9,17-trimethyl derivative (3) adopts a Crown conformation (11) in the solid state. Dynamic n.m.r. spectroscopy indicates that both the 1,9-dimethyl-17-benzyl- (2) and 1,9,17-trimethyl- (3) derivatives exist as interconverting mixtures of Crown (11) and Saddle (12) conformations with the former predominating at equilibrium in solution.

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Synthesis and conformational behaviour of 1,9,17-triaza[2.2.2]metacyclophane-2, 10, 18-trione derivatives

Abstract

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