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.
Copyright:
Copyright 2015 Elsevier B.V., All rights reserved.
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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U2 - 10.1039/P19820001715
DO - 10.1039/P19820001715
M3 - Article
AN - SCOPUS:37049108435
SP - 1715
EP - 1720
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
SN - 0300-922X
ER -