ChemInform Abstract: SYNTH. VON ALIPHATISCHEN UND AROMATISCHEN DIAMINEN DURCH RK. VON ALKYLPHOSPHATEN MIT DEN ENTSPRECHENDEN PRIMAEREN AMINEN

Friedmann, Gilbert; Brini, Mathilde; Ederle, Pierre; Gasser, Jean; Holderith, Paul‐Joseph; Vernois, Michel; Widmaier, Jean‐Michel

doi:10.1002/chin.197026210

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“…This transfer yields an equivalent amount of internal salt 13. Compound 13 and related dimethybenzimidazolium salts are capable of effecting intermolecular methylations (16), ultimately leading to the formation of bis(benzimidazo1e) 15, as well as to N,N,Nf-trimethyl-1,2-benzenediamine and N,N, Nf,N'-tetramethyl-1 ,2-benzenediamine (17), which are both detected in low yields among the products of pyrolysis. Support for this hypothesis is provided by the observation that a similar pyrolysis of internal salt 13 in the presence of two molar equivalents of N,N'-dimethyl-1,2-benzenediamine yielded bis(benzimidazo1e) 15 and N,N,N'-trimethyl-l,2-benzenediamine as major products.…”

Section: Resultsmentioning

confidence: 99%

Formal transfers of hydride from carbon–hydrogen bonds. Attempted generation of H₂ by intramolecular protonolyses of the activated carbon–hydrogen bonds of dihydrobenzimidazoles

Brunet¹,

Wuest²

1996

Can. J. Chem.

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Protonolyses of carbon-hydrogen bonds can occur under suitable conditions to produce carbocations and H,. In an effort to accelerate these fundamental reactions, we have attempted to make them intramolecular by devising compounds in which carbon-hydrogen bonds designed to be particularly good formal donors of hydride are held in close proximity to acidic sites. Dihydrobenzimidazoles 4 and 11 are compounds of this type, since the carbon-hydrogen bonds at C2 are activated as formal donors of hydride by adjacent lone pairs in a dihydroaromatic ring, and acidic anilinium and carboxylic acid groups are held nearby. Unfortunately, this proximity does not lead to the formation of Hz by protonolysis; instead, other reactions intervene when compounds 4 and 11 are subjected to pyrolysis.Key words: intramolecular protonolysis of carbon-hydrogen bonds, formal donors of hydride, generation of H,, dihydrobenzimidazoles.RksumC : La protonolyse des liaisons carbone-hydrogkne peuvent se produire dans des conditions approprikes pour conduire i des carbocations et du H,. Dans le but d'accC1krer les vitesses de ces rkactions fondamentales, on a essay6 de faire des rCactions intramolkculaires en construisant des composts dans lesquels des liaisons carbone-hydrogkne comportant des donneurs formels d'hydrures particulikrement bons seront maintenues faible distance des sites acides. Les dihydrobenzimidazoles 4 et 11 sont des composCs de ce type puisque les liaisons carbone-hydrogkne en C(2) sont activCes comme donneurs formels d'hydrure par les paires non partagkes adjacentes du noyau dihydroaromatique alors que les groupes acides anilinium et acide carboxylique sont maintenus B proximitk. Malgrk cette proximitk, la protonolyse ne conduit malheureusement pas h la formation de H,; quand les composks 4 et 11 sont soumis a une pyrolyse, il y a plutBt intervention d'autres reactions.Mots c l b : protonolyse intramolCculaire de liaisons carbone-hydrogkne, donneurs formels d'hydrure, gknkration de H,, dihydrobenzimidazoles.[Traduit par la rCdaction]

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Section: Resultsmentioning

confidence: 99%

Formal transfers of hydride from carbon–hydrogen bonds. Attempted generation of H₂ by intramolecular protonolyses of the activated carbon–hydrogen bonds of dihydrobenzimidazoles

Brunet¹,

Wuest²

1996

Can. J. Chem.

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ChemInform Abstract: SYNTH. VON ALIPHATISCHEN UND AROMATISCHEN DIAMINEN DURCH RK. VON ALKYLPHOSPHATEN MIT DEN ENTSPRECHENDEN PRIMAEREN AMINEN

Abstract: Die prim. Diamine (I) reagieren mit den Estern (II) bei 150‐200° in 8 bis 20 Std. zu den tertiären Diaminen (III) (11‐56% Ausbeute), deren Strukturen IR‐ und NMR‐spektroskopisch bestätigt werden.

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Formal transfers of hydride from carbon–hydrogen bonds. Attempted generation of H₂ by intramolecular protonolyses of the activated carbon–hydrogen bonds of dihydrobenzimidazoles

Formal transfers of hydride from carbon–hydrogen bonds. Attempted generation of H₂ by intramolecular protonolyses of the activated carbon–hydrogen bonds of dihydrobenzimidazoles

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ChemInform Abstract: SYNTH. VON ALIPHATISCHEN UND AROMATISCHEN DIAMINEN DURCH RK. VON ALKYLPHOSPHATEN MIT DEN ENTSPRECHENDEN PRIMAEREN AMINEN

Abstract: Die prim. Diamine (I) reagieren mit den Estern (II) bei 150‐200° in 8 bis 20 Std. zu den tertiären Diaminen (III) (11‐56% Ausbeute), deren Strukturen IR‐ und NMR‐spektroskopisch bestätigt werden.

Cited by 1 publication

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Formal transfers of hydride from carbon–hydrogen bonds. Attempted generation of H2 by intramolecular protonolyses of the activated carbon–hydrogen bonds of dihydrobenzimidazoles

Formal transfers of hydride from carbon–hydrogen bonds. Attempted generation of H2 by intramolecular protonolyses of the activated carbon–hydrogen bonds of dihydrobenzimidazoles

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Formal transfers of hydride from carbon–hydrogen bonds. Attempted generation of H₂ by intramolecular protonolyses of the activated carbon–hydrogen bonds of dihydrobenzimidazoles

Formal transfers of hydride from carbon–hydrogen bonds. Attempted generation of H₂ by intramolecular protonolyses of the activated carbon–hydrogen bonds of dihydrobenzimidazoles