The Brominative Decarboxylation of Optically Active Silver trans-1,2-Cyclohexanedicarboxylate

Applequist, Douglas E.; Werner, Newton D.

doi:10.1021/jo01036a010

Cited by 48 publications

(29 citation statements)

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“…Acid 2 was resolved with quinine according to the literature method. 13 Diffraction quality co-crystals of apy with optically active dicarboxylic acids 1 and 2 were grown from ethanol at ambient temperature using a 1:1 molar ratio of components. The X-ray structure of the complex (S,S)-1Áapy revealed that the crystals (space group P2 1 2 1 2 1 ) (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…16 Compound (S,S)-2 was obtained by resolution of the racemate with quinine according to the reported procedure. 13 The solid state CD spectra were taken with freshly prepared KBr disks and recorded with a Jasco J-715 dichrograph. A mixture of 2-5 mg of the sample and 250 mg of dried KBr was ground and formed into a disk having a thickness of 0.5 mm and a radius of 15 mm.…”

Section: Methodsmentioning

confidence: 99%

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Generation of chirality in 4,4′-azopyridine by co-crystallization with optically active dicarboxylic acids

Wasilewska

Milewska

Gdaniec

et al. 2009

Tetrahedron: Asymmetry

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Generation of chirality in 4,4′-azopyridine by co-crystallization with optically active dicarboxylic acids

Wasilewska

Milewska

Gdaniec

et al. 2009

Tetrahedron: Asymmetry

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“…15 Quinine salt was recrystallized from 95% ethanol. Free ( + )-diacid isolated from the quinine salt was recrystallized from water again (mp 180-180.50C (lit., 16 + 19.4° (c= l.0gdl-1 in acetone)).…”

Section: Methodsmentioning

confidence: 99%

Chromatographic Optical Resolution of Enantiomers on Polyamides Containing 1,2-Disubstituted Cyclohexane Moiety as a Chiral Residue

Nagamura

Fukumoto

Hatäda

1991

Polym J

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ABSTRACT:Optically active polyamides having ( -)-1,2-trans-diaminocyclohexane [( -)-DA] or ( + )-1,2-trans-cyclohexane dicarboxylic acid [( + )-CDA] residue in main chain were synthesized by polycondensation. Polyamides with a p-phenylene group in main chain showed better resolution for several racemic compounds than the polyamides with a polymethylene group [ fCH 2:);; (n=2-7)] in main chain. Among the polyamides with a polymethylene group in main chain, the polyamides with a shorter polymethylene group showed better chiral recognition abilities than the polyamides with a longer polymethylene group. Polyamides derived from ( -)-trans-3,6-endomethylene-1,2,3,6-tetrahydrophtharic acid [( -)-ETHF] showed low chiral recognition ability. CD spectra of these polyamides showed characteristic patterns. Odd-even effect was observed in CD spectra of the polyamides having a series of a polymethylene group.

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“…auch die Strukturanalyse des 1,1,2-Tris(N-morpholino)athylens [24] sowie die kiirzlich erschienene systematische Studie iiber die Rontgenstruktur von Enaminen mit tetrasubstituierter Doppelbindung [25]. 24,7" (c = 6,4,Benzol;[7a]: +25,0"). 16) Flukaprakt., 6Oproz.…”

Section: -2 3 ( 5 )unclassified

Struktur eines O, N‐Ketenacetals: (1 RS, 8 SR, 10 SR, 4(15)Z)‐4‐äthyliden‐5‐oxa‐3‐azatricyclo [8.4.0.0^3,8]tetradecan

Kümin

Maverick

Seiler

et al. 1980

Helvetica Chimica Acta

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3 1.III.80) Structure of a 0,N-Keteneacetal: (1 RS,SSR, 10SR,4(15)2)-4-Ethylidene5-oxa-3-azatricyclo [S.4.O.O3*~tetradecane') SummaryMethods for the preparation of a series of model compounds which were required for stereochemical studies are described: the tricyclic 0, N-keteneacetal 1, the two diastereomeric bicyclic amino acids 7 and 10 (see Scheme Z), and the two diastereomeric conformationally fixed tetrahydro-1 ,3-oxazines (= 1,3-0xazixanes) 9 and 11. An x-ray analysis of racemic 1 reveals a quasi-tetrahedral nitrogen pyramid of the 0, N-ketene acetal grouping, and an almost perfect conformational analogy between the N-and C-centered allylic positions at the double bond.Im Rahmen von Untersuchungen iiber die Stereochemie allylischer Reaktionen [ 1-31 haben wir die Titelsubstanz 1 sowohl als (1 S , 8 R , 10 R)-Enantiomer wie auch als Racemat synthetisiert. Es ist gelungen, vom tiefschmelzenden Racemat der gegeniiber Spuren von Luftfeuchtigkeit ausserst instabilen Verbindung eine Rontgenstrukturanalyse durchzufuhren, und hieraus haben sich iiber die primar angestrebte Konfigurationsbestatigung hinaus wertvolle Einblicke in strukturelle Details der 0, N-Ketenacetalgruppierung ergeben. Diese Ergebnisse werden hier mitgeteilt; sie stellen eine Erganzung der kiirzlich iiber die Struktur von Enaminen [4] publizierten Daten dar.

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The Brominative Decarboxylation of Optically Active Silver trans-1,2-Cyclohexanedicarboxylate

Cited by 48 publications

References 0 publications

Generation of chirality in 4,4′-azopyridine by co-crystallization with optically active dicarboxylic acids

Generation of chirality in 4,4′-azopyridine by co-crystallization with optically active dicarboxylic acids

Chromatographic Optical Resolution of Enantiomers on Polyamides Containing 1,2-Disubstituted Cyclohexane Moiety as a Chiral Residue

Struktur eines O, N‐Ketenacetals: (1 RS, 8 SR, 10 SR, 4(15)Z)‐4‐äthyliden‐5‐oxa‐3‐azatricyclo [8.4.0.0^3,8]tetradecan

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The Brominative Decarboxylation of Optically Active Silver trans-1,2-Cyclohexanedicarboxylate

Cited by 48 publications

References 0 publications

Generation of chirality in 4,4′-azopyridine by co-crystallization with optically active dicarboxylic acids

Generation of chirality in 4,4′-azopyridine by co-crystallization with optically active dicarboxylic acids

Chromatographic Optical Resolution of Enantiomers on Polyamides Containing 1,2-Disubstituted Cyclohexane Moiety as a Chiral Residue

Struktur eines O, N‐Ketenacetals: (1 RS, 8 SR, 10 SR, 4(15)Z)‐4‐äthyliden‐5‐oxa‐3‐azatricyclo [8.4.0.03,8]tetradecan

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Struktur eines O, N‐Ketenacetals: (1 RS, 8 SR, 10 SR, 4(15)Z)‐4‐äthyliden‐5‐oxa‐3‐azatricyclo [8.4.0.0^3,8]tetradecan