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2
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33845183717
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Tetrabromo cavitand 2(21% from resorcinol, dihydrocinnamaldehyde, and CHjBrCl, three steps) was metalated in THF with BuLi (-78 °C, 2 min), and N-formylmorpholine was added to give tetraaldehyde 3, 75% (ref 5). A 2:1 molar ratio of 1,3-diaminobenzene to 3 in dry pyridine was stirred under argon at ~65 eC (4 days), the solvent was evaporated, and 1 was purified by chromatography (silica gel, R1 0.29, CH2C12,45% yield, mp 240 eC dec).The sum of the elemental analyses (C, N, O) of dried 1 (ref 5) was 100.13%. The FAB MS of 1 gave the molecular ion (+ H+, 100%). All 500-MHz spectral protons of 1 except those of the eight pendant C6H5 groups were assigned by a homonuclear correlation COSY experiment (we thank Dr.Mike Gekel for help). NOE experiments (Derome, A. E. Modern NMR Techniques for Chemistry Research, Pergamon Press: Oxford, 1987; p 97)were performed on 1 in CDC13. Irradiation of H* of 1 gave a -2% enhancementof Hb, whereas irradiation of Hb produced a -3% enhancement of H1, but irradiation of Hc had no effect on H*. Thus all eight configurations about the CN bonds have Hb and the aryl syn to one another
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Tetrabromo cavitand 2 (Sherman, J. C.; Cram, D. J. J. Am. Chem.Soc. 1989, III, 4527–4528) (21% from resorcinol, dihydrocinnamaldehyde, and CHjBrCl, three steps) was metalated in THF with BuLi (-78 °C, 2 min), and N-formylmorpholine was added to give tetraaldehyde 3, 75% (ref 5). A 2:1 molar ratio of 1,3-diaminobenzene to 3 in dry pyridine was stirred under argon at ~65 eC (4 days), the solvent was evaporated, and 1 was purified by chromatography (silica gel, R1 0.29, CH2C12,45% yield, mp 240 eC dec).The sum of the elemental analyses (C, N, O) of dried 1 (ref 5) was 100.13%. The FAB MS of 1 gave the molecular ion (+ H+, 100%). All 500-MHz spectral protons of 1 except those of the eight pendant C6H5 groups were assigned by a homonuclear correlation COSY experiment (we thank Dr.Mike Gekel for help). NOE experiments (Derome, A. E. Modern NMR Techniques for Chemistry Research, Pergamon Press: Oxford, 1987; p 97)were performed on 1 in CDC13. Irradiation of H* of 1 gave a -2% enhancementof Hb, whereas irradiation of Hb produced a -3% enhancement of H1, but irradiation of Hc had no effect on H*. Thus all eight configurations about the CN bonds have Hb and the aryl syn to one another
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(1989)
J. Am. Chem.Soc.
, vol.III
, pp. 4527-4528
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Sherman, J.C.1
Cram, D.J.2
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3
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85023412376
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This paper is based on the Ph.D. Thesis of Dr. M. L. C. Quan: Three New Classes of Hosts. Glycoside-Binding Hosts, Carcerands and Hemicarcerands University of California at Los Angeles, Chapter III
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This paper is based on the Ph.D. Thesis of Dr. M. L. C. Quan: Three New Classes of Hosts. Glycoside-Binding Hosts, Carcerands and Hemicarcerands, University of California at Los Angeles, 1990, Chapter III, pp 93–171.
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(1990)
, pp. 93-171
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4
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85023412210
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Full documentation and discussion is found in this thesis, available to the public through University Microfilms International, 300 North Zeeb Road, Ann Arbor, MI 48
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Full documentation and discussion is found in this thesis, available to the public through University Microfilms International, 300 North Zeeb Road, Ann Arbor, MI 48 106–1346.
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6
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0000353811
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Tanner, M. E.; Knobter, C. B.; Cram, D. J. J. Am. Chem. Soc. 1990, 112, 1659–1660.
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(1990)
J. Am. Chem. Soc.
, vol.112
, pp. 1659-1660
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Tanner, M.E.1
Knobter, C.B.2
Cram, D.J.3
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8
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85023361130
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Under the latter conditions, [3.3]paracyclophane, 9,10-dimethoxyanthracene,9,10-dimethylanthracene, dibenzenechromium, carboranes (1,7-C2BioH12 and l,10-C2B8Hlo), and tetrabutyl phosphate failed to form complexes detectable by NMR.
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Under the latter conditions, [3.3]paracyclophane, 9,10-dimethoxyanthracene,9,10-dimethylanthracene, dibenzenechromium, carboranes (1,7-C2BioH12 and l,10-C2B8Hlo), and tetrabutyl phosphate failed to form complexes detectable by NMR.
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