Heterocycles from ketenimines. VI. A perhydro‐<i>s</i>‐triazine through thermolysis

Barker, Marvin W.; Rosamond, James D.

doi:10.1002/jhet.5570090642

Cited by 6 publications

(2 citation statements)

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“…A few examples of thermal reactions of ketenimines were known and their oligomerization gave the dimers [l], trimers [2], and quinazolines [3] arising from the cyclization across C = C or C = N bonds of cumulene groups of ketenimines. In the course of our study of functionalized heterocumulenes as the building blocks of heterocycles, we found [4] the novel cyclization of N-phenylcarbethoxy-(pheny1thio)ketenimine (I) affording 2-ethoxy-3-phenylthio-4-quinolinol (11) (Scheme I).…”

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confidence: 99%

2‐Alkoxy‐3‐substituted‐4‐quinolinols from the thermal reactions of N‐phenylketenimines bearing ester groups

Motoyoshiya

Takagi

Hirakawa

et al. 1986

Journal of Heterocyclic Chem

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confidence: 99%

2‐Alkoxy‐3‐substituted‐4‐quinolinols from the thermal reactions of N‐phenylketenimines bearing ester groups

Motoyoshiya

Takagi

Hirakawa

et al. 1986

Journal of Heterocyclic Chem

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“…Ketene imines are known to dimerize [1±5] and trimerize [6] to yield heterocyclic compounds whose structures depend on the ketene imine substitution pattern and reaction condition. For example, Barker and Rosamond [2] reported that when diphenylketene N-methylimine is heated for 1 week at 125°C, the azetidine 1, an unsymmetrical dimer results.…”

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confidence: 99%

Ab initio studies on the mechanism of dimerization reactions of ketene imine and bis(trifluoromethyl)ketene imine

Wang

Fang

1999

Theoretical Chemistry Accounts: Theory, Computation, and Modeli

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The dimerization reactions of ketene imine and bis(tri¯uoromethyl)ketene imine were studied theoretically. All the dimerization processes take place in a concerted but asynchronous manner, each proceeding through a four-membered ring transition state. For the ketene imine dimerization reactions, three dierent processes have almost equal activation barriers, while for the three bis(tri¯uoromethyl)ketene imine dimerization processes the reaction giving symmetrical a four-membered heterocyclic product has the lowest activation barrier.

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Fully Reversible Cyclic Dimerization of Diphosphanylketenimines Promoted by Intramolecular C−H⋅⋅⋅N Hydrogen Bonds

et al. 2000

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Einfach bei der Kristallisation bei Raumtemperatur reagiert das Diphosphanylketenimin 1 zum unsymmetrischen Dimer 2, und zwar über eine neuartige [2+3]‐Cycloaddition; einer der beiden Phosphanylsubstituenten ist an der Anellierung beteiligt. Diese Dimerisierung ist vollständig reversibel und scheint durch die Bildung intramolekularer CH⋅⋅⋅N‐Wasserstoffbrückenbindungen gefördert zu werden.

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Heterocycles from ketenimines. VI. A perhydro‐s‐triazine through thermolysis

Cited by 6 publications

References 10 publications

2‐Alkoxy‐3‐substituted‐4‐quinolinols from the thermal reactions of N‐phenylketenimines bearing ester groups

2‐Alkoxy‐3‐substituted‐4‐quinolinols from the thermal reactions of N‐phenylketenimines bearing ester groups

Ab initio studies on the mechanism of dimerization reactions of ketene imine and bis(trifluoromethyl)ketene imine

Fully Reversible Cyclic Dimerization of Diphosphanylketenimines Promoted by Intramolecular C−H⋅⋅⋅N Hydrogen Bonds

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