„Aktivierung”︁ N‐haltiger Heterocyclen durch Silylierung

Birkofer, Leonhard; Richter, Paul; Ritter, A.

doi:10.1002/cber.19600931207

Cited by 149 publications

(21 citation statements)

References 8 publications

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“…However, l a was oxidized by sulfur in (1)(2)(3)(4)(5)(6)(7)(8)(9) (Fig. 1) which are of interest as potential refluxing benzene, to form 46.…”

Section: Resultsmentioning

confidence: 99%

Syntheses of Some Phosphino- and Phosphinatoazoles

Fischer¹,

Peterson²,

Nixon³

1974

Can. J. Chem.

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The following N-substituted azoles have been prepared: (a) diphenylphosphine derivatives of pyrazole (la), 3,5,-dimethylpyrazole (lb), 3(5)-methylpyrazole (isomers 2a and 2b), pyrrole (7), imidazole (8), and 1,2,4-triazole (9); (b) diphenylphosphinatopyrazole (46); (c) dichlorophosphinopyrazole (5a) and dichlorophosphino-3,5-dimethylpyrazole (Sb); (c) 1,l-phenylphosphinobis(pyrazo1e) (3); (d) tris (pyrazoly1) 3); ( e ) tris(pyrazoly1)phosphine (6a) et le tris(dimethy1-3,y pyrazoly1)phosphine (6b). Les methodes de synthese font appel aux reactions (i-ic): (i) l'azole avec la chlorophosphine (pour 1-3, 8, 9) ou +,P(O)Cl (4a) dans une solution Ctheree avec la triethylamine comme accepteur d'acide halogene-hydrique; (ii) la trimCthylsilylazole avec le trichlorure de phosphore (5, 6 ) ; (iii) le pyrrolidure de potassium avec la diphtnylchlorophosphine (8); (it.) l'oxydation du soufre de l a (4b). Les attributions spectrales deduites de 1'Ctude r.m.n. sont discutees.[Traduit par le journal]

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“…However, l a was oxidized by sulfur in (1)(2)(3)(4)(5)(6)(7)(8)(9) (Fig. 1) which are of interest as potential refluxing benzene, to form 46.…”

Section: Resultsmentioning

confidence: 99%

Syntheses of Some Phosphino- and Phosphinatoazoles

Fischer¹,

Peterson²,

Nixon³

1974

Can. J. Chem.

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“…Compounds 1,4,and 6 showed no broadening of the lines at 150°C but 2 and 3 showed broadening at 130°C. In the case of 5 , no exchange was observed at 125°C.…”

Section: N-(tert-b~ii~~ldin?eth~lsilyl)ir?ziclzole Arzdmentioning

confidence: 93%

N-(tert-Butyldimethylsilyl)imidazole and related heterocycles: ¹³C nuclear magnetic resonance study and reaction with dimethylsulfoxide

Janzen¹,

Lypka²,

Wasylishen³

1980

Can. J. Chem.

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N-tert-Butyldimethylsilyl derivatives of imidazole, 2-methylimidazole, 4-methylimidazole, benzimidazole, pyrazole, 1,2,4-triazole, and benzotriazole were prepared from tert-butyldimethylsilyl chloride and the corresponding heterocyclic compound. The products were identified by carbon and proton nmr, mass spectrometry, and elemental analysis. The carbon nmr spectra confirmed the absence of intermolecular silyl exchange at ambient temperature. Silyl exchange did occur at elevated temperatures, 130–160 °C.Reaction of N-tert-butyldimethylsilyl or N-trimethylsilyl heterocycles with dimethylsulfoxide gave N-(methylthio)methyl derivatives of imidazole, 2-methylimidazole, 4-methylimidazole, benzimidazole, pyrazole, and 1,2,4-triazole. The products were characterized by carbon and proton nmr, mass spectrometry, and elemental analysis. A mechanism involving a Pummerer rearrangement is proposed to account for the results.

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“…The pyrrolyl anion is also easily converted into the corresponding 1-silylated pyrroles by treatment with triisopropylsilyl chloride (TIPSCl) [244] or tert-butyldimethylsilyl chloride (TBSCl) [385], as well as with other trialkylsilyl chlorides [386]. The high reactivity of the pyrrolyl anion is neatly demonstrated by the reaction of pyrrolylsodium with hexafluorobenzene, which gives hexa(pyrrol-1-yl)benzene via a S N Ar mechanism [387].…”

Section: Reactivity J313mentioning

confidence: 97%

Five‐Membered Heterocycles: Pyrrole and Related Systems

Bergman

Janosik

2011

Modern Heterocyclic Chemistry

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„Aktivierung”︁ N‐haltiger Heterocyclen durch Silylierung

Abstract: Pyrrolidin undPiperidin wurden vorher iibcr Natrium getrocknet.

Cited by 149 publications

References 8 publications

Syntheses of Some Phosphino- and Phosphinatoazoles

Syntheses of Some Phosphino- and Phosphinatoazoles

N-(tert-Butyldimethylsilyl)imidazole and related heterocycles: ¹³C nuclear magnetic resonance study and reaction with dimethylsulfoxide

Five‐Membered Heterocycles: Pyrrole and Related Systems

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„Aktivierung”︁ N‐haltiger Heterocyclen durch Silylierung

Abstract: Pyrrolidin undPiperidin wurden vorher iibcr Natrium getrocknet.

Cited by 149 publications

References 8 publications

Syntheses of Some Phosphino- and Phosphinatoazoles

Syntheses of Some Phosphino- and Phosphinatoazoles

N-(tert-Butyldimethylsilyl)imidazole and related heterocycles: 13C nuclear magnetic resonance study and reaction with dimethylsulfoxide

Five‐Membered Heterocycles: Pyrrole and Related Systems

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N-(tert-Butyldimethylsilyl)imidazole and related heterocycles: ¹³C nuclear magnetic resonance study and reaction with dimethylsulfoxide