1965
DOI: 10.1039/jr9650001685
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316. The structure of cyclotriveratrylene (10,15-dihydro-2,3,7,8,12,13-hexamethoxy-5H-tribenzo[a,d,g]cyclononene) and related compounds

Abstract: hexamethoxy-5H-tribenzo[a,d,g]cyclononene) and Related CornpoundsBy A. S. LINDSEYThe product of condensation of veratrole and formaldehyde under acid conditions is shown to be a cyclic trimer possessing a novel ring system (I; R = Me). Three general methods of preparing this compound and its analogues are examined and their trimeric nature is established. Certain aspects of the stereochemical conformation of cyclotriveratrylene are discussed.

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Cited by 90 publications
(38 citation statements)
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“…Captopril (≥98 %, Cambridge Biosciences Ltd., Cambridge, UK), graphite powder (>20 µm synthetic, Sigma‐Aldrich, Dorset, UK), boric acid (99.5 %, Sigma‐Aldrich, Dorset, UK), phosphoric acid (85 wt%, Sigma‐Aldrich, Dorset, UK), acetic acid (99.5 %, BDH, Poole, UK), citric acid (98 %, BDH, Poole, UK), sodium citrate (98 %, Sigma, Dorset, UK), potassium dihydrogen phosphate (≥99 %, Sigma‐Aldrich, Dorset, UK), potassium monohydrogen phosphate (≥98 %, Sigma‐Aldrich, Dorset, UK), sodium carbonate (ACS grade, BDH, Poole, UK), sodium bicarbonate (99.7 %, Sigma, Dorset, UK), and potassium chloride (99 %, Sigma‐Aldrich, Dorset, UK) were all purchased and as used received without any further purification steps. CTV was synthesized previously according to the method reported by Lindsey 36. Analysis and characterization of the CTV material was reported in a previous paper 24.…”
Section: Methodsmentioning
confidence: 99%
“…Captopril (≥98 %, Cambridge Biosciences Ltd., Cambridge, UK), graphite powder (>20 µm synthetic, Sigma‐Aldrich, Dorset, UK), boric acid (99.5 %, Sigma‐Aldrich, Dorset, UK), phosphoric acid (85 wt%, Sigma‐Aldrich, Dorset, UK), acetic acid (99.5 %, BDH, Poole, UK), citric acid (98 %, BDH, Poole, UK), sodium citrate (98 %, Sigma, Dorset, UK), potassium dihydrogen phosphate (≥99 %, Sigma‐Aldrich, Dorset, UK), potassium monohydrogen phosphate (≥98 %, Sigma‐Aldrich, Dorset, UK), sodium carbonate (ACS grade, BDH, Poole, UK), sodium bicarbonate (99.7 %, Sigma, Dorset, UK), and potassium chloride (99 %, Sigma‐Aldrich, Dorset, UK) were all purchased and as used received without any further purification steps. CTV was synthesized previously according to the method reported by Lindsey 36. Analysis and characterization of the CTV material was reported in a previous paper 24.…”
Section: Methodsmentioning
confidence: 99%
“…-carbonyl]-aminosaureithylestern (2). Bei der Reaktion mit den trigeren Isocyanaten (Ic) und ( I d ) wird 1 Std.…”
Section: Peptid-und Axapeptid-synthesen Mitunclassified
“…Der Substitutionsort am Triazolring ergibt sich aus den NMR-Spektren (aufgenommen in CC14) von (2b) und (2d): In Ubereinstimmung rnit Untersuchungen von H. A. Staub am N-Acetyl-1,2.4triazol 121 beweisen jeweils zwei Protonensignale gleicher Intensitat bei 2,13 und 1,17 t bzw. 2,15 und 1,207 die unsymmetrische Struktur(2) mit ungleichwertigen Triazol Protonen. Die Verbindungen (2a)-(2d) eignen sich wie die entsprechenden Imidazol-Derivate 131 zu Peptidsynthesen.…”
unclassified
“…For the first time, Cyclotriveratrylene (CTV) was synthesised by Gertrude Robinson in 1915 [97] and in 1965, Lindsey identified the correct structure [98]. The host molecule cyclotriveratrylene (CTV) has a relatively rigid bowl shape, creating a molecular cavity, much like those seen in cone conformation calixarenes.…”
Section: Cyclotriveratrylenesmentioning
confidence: 99%