Über die Synthese von Mono‐ und Dicarbonsäureamiden aus Kohlenwasserstoffen und Harnstoffchlorid

Hopff, H.; Ohlinger, Helmut

doi:10.1002/ange.19490610505

Cited by 18 publications

(6 citation statements)

References 4 publications

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“…This is consistent with the appreciable stability of the parent carbamoyl chloride (H 2 NCOCl) [2,3,4] relative to the highly unstable formyl chloride (HOCOCl) [1]. …”

Section: Solvolyses Of N-alkyl-n-arylcarbamoyl Chloridessupporting

confidence: 67%

“…It could be stabilized, prior to subsequent reaction, by forming a molecular complex with AlCl 3 or FeCl 3 . These complexes can then be reacted with aromatic hydrocarbons to give acid amides in about 90% yields [2]. Olah [85] has investigated the complexes formed with Lewis Acids (such as with AlCl 3 or FeCl 3 [2]) by carbamoyl chlorides or fluorides and found that the complexing involves coordination with the carbonyl oxygen.…”

Section: Reactions Of Monosubstituted and Unsubstituted Carbamoyl mentioning

confidence: 99%

“…These complexes can then be reacted with aromatic hydrocarbons to give acid amides in about 90% yields [2]. Olah [85] has investigated the complexes formed with Lewis Acids (such as with AlCl 3 or FeCl 3 [2]) by carbamoyl chlorides or fluorides and found that the complexing involves coordination with the carbonyl oxygen. Similarly, the protonation of carbamoyl fluorides, including the parent, by FSO 3 H or FSO 3 H-SbF 5 also takes place at the carbonyl oxygen.…”

Section: Reactions Of Monosubstituted and Unsubstituted Carbamoyl mentioning

confidence: 99%

“…In contrast to the parent acid of chloroformate esters (HOCOCl), where attempts to prepare it lead to carbon dioxide and hydrogen chloride [1], the corresponding parent structure for carbamoyl chlorides (H 2 NCOCl) is a stable molecule, even at quite high temperatures [2,3,4]. It can be stabilized further by complexation with aluminum chloride or iron (III) chloride [2].…”

Section: Introductionmentioning

confidence: 99%

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Mechanistic Studies of the Solvolyses of Carbamoyl Chlorides and Related Reactions

D’Souza

Kevill

2016

IJMS

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Carbamoyl chlorides are important intermediates, both in the research laboratory and in industrial scale syntheses. The most studied and used are the disubstituted derivatives, incorporating either aryl or alkyl groups (Ar2NCOCl or R2NCOCl). Sometimes, the groups are tied back to give a ring and piperidino- and morpholino-derivatives are commonly encountered. Some studies have been made with two different groups attached. Solvolyses tend to occur at the carbonyl carbon, with replacement of the chloride ion. Studies of both rate and products are reviewed and the solvolysis reactions are usually SN1, although addition of an amine leads to a superimposable bimolecular component. Many of the studies under solvolytic conditions include the application of the extended Grunwald–Winstein equation. The monosubstituted derivatives (ArNHCOCl or RNHCOCl) are less studied. They are readily prepared by the addition of HCl to an isocyanate. In acetonitrile, they decompose to set up and reach equilibrium with the isocyanate (ArNCO or RNCO) and HCl. Considering that the structurally related formyl chloride (HOCOCl) is highly unstable (with formation of HCl + CO2), the unsubstituted carbamoyl chloride (H2NCOCl) is remarkably stable. Recommended synthetic procedures require it to survive reaction temperatures in the 300–400 °C range. There has been very little study of its reactions.

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“…This is consistent with the appreciable stability of the parent carbamoyl chloride (H 2 NCOCl) [2,3,4] relative to the highly unstable formyl chloride (HOCOCl) [1]. …”

Section: Solvolyses Of N-alkyl-n-arylcarbamoyl Chloridessupporting

confidence: 67%

Section: Reactions Of Monosubstituted and Unsubstituted Carbamoyl mentioning

confidence: 99%

Section: Reactions Of Monosubstituted and Unsubstituted Carbamoyl mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Mechanistic Studies of the Solvolyses of Carbamoyl Chlorides and Related Reactions

D’Souza

Kevill

2016

IJMS

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“…ml Methylenchlorid wurde bei 0" inncrt 30 Min. mit einer Losung yon 50 g (0,237 Mol) Harnstoffchlorid-Aluminiumchlorid-Komplex[26] in 300 ml Ather-Methylenchlorid 2 : 1 versetzt. Der Ansatz wurde 48 Std.…”

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Welkstoffe und Antibiotika. 30. Mitteilung. Ausgangsprodukte zur Totalsynthese des Javanicins

Hardegger

Steiner

Widmer

et al. 1964

Helvetica Chimica Acta

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Zur Herstellung von Ausgangsprodukten zur Synthese des Javanicins wurden, ausgehend von Vanillin (1) über Methoxyhydrochinon (2), dessen Ester 2a, b und 1, 2, 4‐Trimethoxybenzol (2c) mit FRIES'scher Verschiebung, FRIEDEL‐CRAFTS‐Reaktion und MANNICH‐Kondensation eine grössere Anzahl Verbindungen vom Typus 3, 4, 5, 6 hergestellt, welche die neu eingeführten Substituenten in o‐, m‐, p‐Stellung zu den bereits vorhandenen Sauerstoff‐Funktionen tragen. Weitere Auf‐baureaktionen unter Anwendung von Malonestersynthesen führten zu monocyclischen Präparaten von Typus 20, 21, die z. T. bereits sämtliche C‐ und O‐Atome des Javanicins in der richtigen Anordnung aufwiesen, bisher aber nicht zu Javanicin‐Derivaten cyclisiert werden konnten.

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Synthesis of amides

Beckwith

1970

PATAI'S Chemistry of Functional Groups

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Über die Synthese von Mono‐ und Dicarbonsäureamiden aus Kohlenwasserstoffen und Harnstoffchlorid

Cited by 18 publications

References 4 publications

Mechanistic Studies of the Solvolyses of Carbamoyl Chlorides and Related Reactions

Mechanistic Studies of the Solvolyses of Carbamoyl Chlorides and Related Reactions

Welkstoffe und Antibiotika. 30. Mitteilung. Ausgangsprodukte zur Totalsynthese des Javanicins

Synthesis of amides

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