Zur Konfigurationsbestimmung einiger O‐Acylacethydroximsäuremethylester durch Messung des Dipolmomentes

Ketz, Ernst‐Ulrich; Zinner, G.

doi:10.1002/ardp.19783110613

Cited by 6 publications

(3 citation statements)

References 14 publications

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“…Their steric arrangement could be determined from dipole moments 123,124 when previous experience on similar compounds was exploited. In 35 the conformation on N O was assumed ap as it is uniformly in all derivatives of this type; also the conformation sp on C O in the ester group is beyond discussion.…”

Section: Conjugated Systems X−c=n−ymentioning

confidence: 99%

Dipole Moments of Compounds Containing Double Bonds

Exner

2009

Patai's Chemistry of Functional Groups

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Introduction Progress in the Dipole Moment Method C  C Bonds C  N Bonds C  O Bonds C  S Bonds C  P Bonds Other Double Bonds

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Section: Conjugated Systems X−c=n−ymentioning

confidence: 99%

Dipole Moments of Compounds Containing Double Bonds

Exner

2009

Patai's Chemistry of Functional Groups

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Introduction Progress in the Dipole Moment Method C  C Bonds C  N Bonds C  O Bonds C  S Bonds C  P Bonds Other Double Bonds

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“…CH,); 24.1 (4,CH, Ethyl Chloroacetohydroximate (28). The procedure of Ketz and Zinner [34] was modified as follows: a soh. of ethyl chloroacetimidate hydrochloride (15.70 g, 0.10 mol) in EtzO (100 ml) was added at 0" to a soln.…”

Section: Experimental Partmentioning

confidence: 99%

“…69 (1 986) Scheme 2). The hydroximo ethers 2 S 3 0[34] [35] are easily available from the corresponding imidates[36]. The thermal stability of 25-27 is low and decreases in the sequence 25-27.…”

mentioning

confidence: 99%

Diastereoselectivity and Reactivity in the Diels‐Alder Reactions of α‐Chloronitroso Ethers

Felber

Kresze

Prewo

et al. 1986

Helvetica Chimica Acta

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~ ~~~The structure of the a-chloronitroso ether I, obtained from the hydroximolactone 2 and tert-butyl hypochlorite (89 %), was established by X-ray crystallographic analysis. The [4 + 2 1 cycloadditions of 1 with the dienes 3 and %I1 led to the N-unsubstituted 3,6-dihydro-2H-1,2-oxazines 6 and 12-16 in high enantiomeric excess ( Table 1). Due to the additional a-alkoxy group, the reactivity of 2 is much superior to the one of known a-chloronitrosoalkanes. The reactive conformation of 1 was deduced from the X-ray analysis as well as the high diastereoselectivity of the cycloadditions. The importance of the a-alkoxy group was evidenced from the similar reactivity of the racemic a-chloronitroso ethers 2 5 2 7 which were prepared from the hydroximo ethers 28-30 and tert-butyl hypochlorite.

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Darstellung von O‐Acylhydroxylaminen mit (E)‐ und (Z)‐Acethydroximsäuremethylester als Schutzfunktion

Ketz

Zinner

1978

Archiv der Pharmazie

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Die (E). und (2)-Form der Titelverbindung 1 eignen sich gleichermden gut als Schutzfunktion zur Darstellung N-unsubstituierter 0-Acylhydroxylamine 3: nach erfolgter Acylierung des Esters mit Saurechloriden, Chlorameisensaureestern und Isocyanaten gelingt ihre Entfernung unabhkgig von der Konfiguration durch eine standardisierte Acidolyse. Synthesis of 0-Acylhydroxylamines with Methyl (E)and /Z)-.Acetohydroximate as ProtectingGroup.The (E)and (ZJ-isomers of methyl acetohydroximate (1) are good protecting groups for synthesizing N-unsubstituted 0-acylhydroxylamines 3: after 0-acylation of the hydroxylamines with acyl chlorides, chloroformates or isocyanates, the protecting groups can be removed by acidolysis, independent of their configuration. 0-Acylierte Hydroxylaminealso 0-Acyloxyamine 3 -mit freier Aminogruppe sind nur in Ausnahmefallen durch direkte Synthesefiihrung zugiinglich'); im allgemeinen bedarf es zu h e r Herstellung der Anwendung einer Schutzfunktion, die in einem letzten Reaktionsschritt nach erfolgter Umsetzung am Sauerstoffatom unter schonenden Bedingungen wieder abgespalten werden kann und leicht vom gewunschten Endprc dukt abtrennbar ist. Diese Funktion erfullt in hohem M d e die Substanzklasse der Acethydroximsaureester 1 (Weg A)'), deren Anwendung wirtschaftlicher und gelegentlich auch in der Reaktionsfuhrung gbnstiger erscheint als die des gleichfalls dafur 1 B. Zeeh und H. Metzga in Houben-Weyl-Miiller, Methoden der Organischen Chemie, 4. Aufl.,

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Zur Konfigurationsbestimmung einiger O‐Acylacethydroximsäuremethylester durch Messung des Dipolmomentes

Cited by 6 publications

References 14 publications

Dipole Moments of Compounds Containing Double Bonds

Dipole Moments of Compounds Containing Double Bonds

Diastereoselectivity and Reactivity in the Diels‐Alder Reactions of α‐Chloronitroso Ethers

Darstellung von O‐Acylhydroxylaminen mit (E)‐ und (Z)‐Acethydroximsäuremethylester als Schutzfunktion

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