Conformational behaviour of medium-sized rings. Part 13. 5,18- dihydro- and 5,11,12,18-tetrahydrotribenzo[b, f, j][1,4]diazacyclodode- cine-6,17-diones

W. David Ollis; Julia Stephanidou Stephanatou; J. Fraser Stoddart

doi:10.1039/P19820001715

Conformational behaviour of medium-sized rings. Part 13. 5,18- dihydro- and 5,11,12,18-tetrahydrotribenzo[b, f, j][1,4]diazacyclodode- cine-6,17-diones

W. David Ollis^*, Julia Stephanidou Stephanatou, J. Fraser Stoddart

^*Corresponding author for this work

Chemistry

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Abstract

The unsaturated (3) and saturated (6) bislactams have been prepared from condensations of o-phenylenediamine with the bisacyl chlorides (1) and (2) derived from trans-stilbene-2,2′-dicarboxylic acid and bibenzyl-2,2′- dicarboxylic acid, respectively. Dynamic¹H n.m.r. spectroscopy demonstrates that the 5,18-dibenzyl derivative (5) of (3) and the 5,18-dimethyl- (7) and 5,18 -dibenzyl- (8) derivatives of (6) adopt enantiomeric non-planar conformations with averaged C₂ symmetry in solution. In the case of the two 5,18-dibenzyl derivatives (5) and (8), ring inversion is shown to be slow (ΔG‡ = 20.4 and 21.1 kcal mol⁻¹, respectively) on the^XH n.m.r. time scale at room temperature and probably involves propeller-like conformations (9a) ⇋ (9b) as the enantiomeric ground- state conformations. Both the 5,18-dimethyl- (7) and -dibenzyl (8) derivatives of the saturated bislactam (6) form 1:1 inclusion compounds, (7) with o-xylene and (8) with ethanol.

Original language	English (US)
Pages (from-to)	1715-1720
Number of pages	6
Journal	Journal of the Chemical Society, Perkin Transactions 1
DOIs	https://doi.org/10.1039/P19820001715
State	Published - 1982

Funding

We gratefully acknowledge financial support (toJ. S. S.) from the State Scholarship Foundation of the Government of Greece and thank the University of Thessaloniki for granting leave of absence to J. S. S. [1/893 Received, 17th June, 19811 REFERENCES Part 12, S. J. Edge, W. D. Ollis, J. S. Stephanatou, and J. F. Stoddart, preceding paper. J. CHEM. soc. PERIUN TRANS. I 1982 a H. M. Powell, Nature, 1952,170, 156; D. Lawton and H. M. Powell, J. Chem. Soc., 1958, 2339. D. J. Williams and D. Lawton, Tetrahedron Lett., 1975, 111. R. Arad-Yellin, S. Brunie, B. S. Green, M. Knossow, and G. Tsoucaris, J. Am. Chem. SOC.,1979, 101, 7529; R.

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General Chemistry

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@article{7d806d1d4eec4fed94a4e89f3eecb3e6,

title = "Conformational behaviour of medium-sized rings. Part 13. 5,18- dihydro- and 5,11,12,18-tetrahydrotribenzo[b, f, j][1,4]diazacyclodode- cine-6,17-diones",

abstract = "The unsaturated (3) and saturated (6) bislactams have been prepared from condensations of o-phenylenediamine with the bisacyl chlorides (1) and (2) derived from trans-stilbene-2,2′-dicarboxylic acid and bibenzyl-2,2′- dicarboxylic acid, respectively. Dynamic1H n.m.r. spectroscopy demonstrates that the 5,18-dibenzyl derivative (5) of (3) and the 5,18-dimethyl- (7) and 5,18 -dibenzyl- (8) derivatives of (6) adopt enantiomeric non-planar conformations with averaged C2 symmetry in solution. In the case of the two 5,18-dibenzyl derivatives (5) and (8), ring inversion is shown to be slow (ΔG‡ = 20.4 and 21.1 kcal mol−1, respectively) on theXH n.m.r. time scale at room temperature and probably involves propeller-like conformations (9a) ⇋ (9b) as the enantiomeric ground- state conformations. Both the 5,18-dimethyl- (7) and -dibenzyl (8) derivatives of the saturated bislactam (6) form 1:1 inclusion compounds, (7) with o-xylene and (8) with ethanol.",

author = "Ollis, \{W. David\} and Stephanatou, \{Julia Stephanidou\} and Stoddart, \{J. Fraser\}",

note = "Funding Information: We gratefully acknowledge financial support (toJ. S. S.) from the State Scholarship Foundation of the Government of Greece and thank the University of Thessaloniki for granting leave of absence to J. S. S. [1/893 Received, 17th June, 19811 REFERENCES Part 12, S. J. Edge, W. D. Ollis, J. S. Stephanatou, and J. F. Stoddart, preceding paper. J. CHEM. soc. PERIUN TRANS. I 1982 a H. M. Powell, Nature, 1952,170, 156; D. Lawton and H. M. Powell, J. Chem. Soc., 1958, 2339. D. J. Williams and D. Lawton, Tetrahedron Lett., 1975, 111. R. Arad-Yellin, S. Brunie, B. S. Green, M. Knossow, and G. Tsoucaris, J. Am. Chem. SOC.,1979, 101, 7529; R. ",

year = "1982",

doi = "10.1039/P19820001715",

language = "English (US)",

pages = "1715--1720",

journal = "Journal of the Chemical Society, Perkin Transactions 1",

issn = "1470-4358",

publisher = "Chemical Society",

}

Conformational behaviour of medium-sized rings. Part 13. 5,18- dihydro- and 5,11,12,18-tetrahydrotribenzo[b, f, j][1,4]diazacyclodode- cine-6,17-diones. / Ollis, W. David; Stephanatou, Julia Stephanidou; Stoddart, J. Fraser.
In: Journal of the Chemical Society, Perkin Transactions 1, 1982, p. 1715-1720.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Conformational behaviour of medium-sized rings. Part 13. 5,18- dihydro- and 5,11,12,18-tetrahydrotribenzo[b, f, j][1,4]diazacyclodode- cine-6,17-diones

AU - Ollis, W. David

AU - Stephanatou, Julia Stephanidou

AU - Stoddart, J. Fraser

N1 - Funding Information: We gratefully acknowledge financial support (toJ. S. S.) from the State Scholarship Foundation of the Government of Greece and thank the University of Thessaloniki for granting leave of absence to J. S. S. [1/893 Received, 17th June, 19811 REFERENCES Part 12, S. J. Edge, W. D. Ollis, J. S. Stephanatou, and J. F. Stoddart, preceding paper. J. CHEM. soc. PERIUN TRANS. I 1982 a H. M. Powell, Nature, 1952,170, 156; D. Lawton and H. M. Powell, J. Chem. Soc., 1958, 2339. D. J. Williams and D. Lawton, Tetrahedron Lett., 1975, 111. R. Arad-Yellin, S. Brunie, B. S. Green, M. Knossow, and G. Tsoucaris, J. Am. Chem. SOC.,1979, 101, 7529; R.

PY - 1982

Y1 - 1982

N2 - The unsaturated (3) and saturated (6) bislactams have been prepared from condensations of o-phenylenediamine with the bisacyl chlorides (1) and (2) derived from trans-stilbene-2,2′-dicarboxylic acid and bibenzyl-2,2′- dicarboxylic acid, respectively. Dynamic1H n.m.r. spectroscopy demonstrates that the 5,18-dibenzyl derivative (5) of (3) and the 5,18-dimethyl- (7) and 5,18 -dibenzyl- (8) derivatives of (6) adopt enantiomeric non-planar conformations with averaged C2 symmetry in solution. In the case of the two 5,18-dibenzyl derivatives (5) and (8), ring inversion is shown to be slow (ΔG‡ = 20.4 and 21.1 kcal mol−1, respectively) on theXH n.m.r. time scale at room temperature and probably involves propeller-like conformations (9a) ⇋ (9b) as the enantiomeric ground- state conformations. Both the 5,18-dimethyl- (7) and -dibenzyl (8) derivatives of the saturated bislactam (6) form 1:1 inclusion compounds, (7) with o-xylene and (8) with ethanol.

AB - The unsaturated (3) and saturated (6) bislactams have been prepared from condensations of o-phenylenediamine with the bisacyl chlorides (1) and (2) derived from trans-stilbene-2,2′-dicarboxylic acid and bibenzyl-2,2′- dicarboxylic acid, respectively. Dynamic1H n.m.r. spectroscopy demonstrates that the 5,18-dibenzyl derivative (5) of (3) and the 5,18-dimethyl- (7) and 5,18 -dibenzyl- (8) derivatives of (6) adopt enantiomeric non-planar conformations with averaged C2 symmetry in solution. In the case of the two 5,18-dibenzyl derivatives (5) and (8), ring inversion is shown to be slow (ΔG‡ = 20.4 and 21.1 kcal mol−1, respectively) on theXH n.m.r. time scale at room temperature and probably involves propeller-like conformations (9a) ⇋ (9b) as the enantiomeric ground- state conformations. Both the 5,18-dimethyl- (7) and -dibenzyl (8) derivatives of the saturated bislactam (6) form 1:1 inclusion compounds, (7) with o-xylene and (8) with ethanol.

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DO - 10.1039/P19820001715

M3 - Article

AN - SCOPUS:37049108435

SN - 1470-4358

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JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

ER -

Conformational behaviour of medium-sized rings. Part 13. 5,18- dihydro- and 5,11,12,18-tetrahydrotribenzo[b, f, j][1,4]diazacyclodode- cine-6,17-diones

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