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

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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 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.

Original languageEnglish (US)
Pages (from-to)1715-1720
Number of pages6
JournalJournal of the Chemical Society, Perkin Transactions 1
DOIs
StatePublished - 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.

ASJC Scopus subject areas

  • General Chemistry

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