Etude de la vibration νCO de cetones α-cyclopropaniques

Pierre, Jean‐Louis; Barlet, R.; Arnaud, Paul

doi:10.1016/0584-8539(67)80122-3

Cited by 9 publications

(3 citation statements)

References 21 publications

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“…Stigmasterol (6) was treated with />-toluenesulfonyl chloride in pyridine to yield the tosylate12 (12) which was then converted to the cyclo ether (13) by methanolysis in the presence of anhydrous potassium acetate.12 Ozonolysis of 13 in methylene chloride-pyridine at -78°followed by zinc-acetic acid work-up afforded the unstable aldehyde13 (14), which was immediately reacted with the phospho-rane1 1 15 in dimethyl sulfoxide to give the desired trans-3a,5-cyclo-6|3-methoxy-5tt-cholesta-22-en-24-one (16).…”

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confidence: 99%

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Stereoselective synthesis of two stereoisomers of demethylgorgosterol

Anderson¹,

Powers²,

Djerassi³

et al. 1975

J. Am. Chem. Soc.

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confidence: 99%

“…These values are in good agreement with the spectral data for other cyclopropyl ketones in the literature. 16•17 The nmr spectrum (100 MHz) exhibited signals at 3.31 ppm (3 H, s, -OCH3), 2.75 (2 H, m, -COCHMe2 and -CHOMe), 1.01 (C-19 methyl), 0.67 (C-18 methyl), and 0.3-0.7 (3 H, m, cyclopropyl). The olefinic protons in 16 are no longer present.…”

mentioning

confidence: 99%

Stereoselective synthesis of two stereoisomers of demethylgorgosterol

Anderson¹,

Powers²,

Djerassi³

et al. 1975

J. Am. Chem. Soc.

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“…La stabilite relativement grande du complexe forme par la cyclohexanone pourrait s'expliquer par l'effet inducteur positif propre du cycle [16].…”

Section: = [A] [D]/[ad] (A = -K ) Et Son Ordonnte 21 I'origine Launclassified

Étude de Complexes Accepteur‐Donneur par Spectrométrie Infrarouge: I. Influence de la Nature du Donneur Carbonylé

Nedden

Duyckaerts

1970

Bulletin des Soc Chimique

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Infrared intensity measurements of the free C = O band have been used to investigate the complex formation between ketones or other carbonylated donors and antimony trichloride in CCl4 solutions using Job's continuous variation method. The dissociation constants of the acceptor‐donor complexes with a 1:1 and 1:2 stoichiometry have been calculated. The sequence of donor basicity based on the 1:1 equilibrium constant is discussed in terms of electronic effects of the substituents R and R.

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Über die σ‐Homologen des o‐Benzochinons

Engelhard

Lüttke

1977

Chem. Ber.

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Es wird die Darstellung und die Strukturbestimmung der beiden Isomeren des Bis-o-homoo-benzochinons 3 a und b und des um einen Cyclopropanring armeren Produkts 2 beschrieben; ihre Stereochemie wird erortert. Die Thermolyse von 3b ergibt als einziges Produkt Benzol. Die spektroskopischen Daten zeigen, daD 3 s und b keine, 2 nur in geringem MaDe chinoide Eigenschaften besitzen; 3 s und b sind cycloaliphatische Diketone. The a-Homologues of o-BenzoquinoneThe preparation and the determination of the structure of the two isomers of bis-u-homo-obenzoquinone 3 a and b and their mono-homo analogue 2 is described and their stereochemistry is discussed. The thermolysis of 3b yields benzene as single product. The spectroscopic data indicate that 3 a and b have no quinonoid properties while they are found to a small extent in 2. 3a and b are best described as cycloaliphatic diketones.Bisherige Untersuchungen an 1 lassen hierzu einen geringen Beitrag der Cyclopropylketon-Teilchromophore erkennen ; die Synthese des Bishomo-o-chinons 3 gewinnt zusatzliches Interesse dadurch, dal3 die Untersuchung der chinoiden Eigenschaften ') M.

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Etude de la vibration νCO de cetones α-cyclopropaniques

Cited by 9 publications

References 21 publications

Stereoselective synthesis of two stereoisomers of demethylgorgosterol

Stereoselective synthesis of two stereoisomers of demethylgorgosterol

Étude de Complexes Accepteur‐Donneur par Spectrométrie Infrarouge: I. Influence de la Nature du Donneur Carbonylé

Über die σ‐Homologen des o‐Benzochinons

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