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Digitale Medien

Borane-Substituted Imidazol-2-ylidenes: Syntheses, Structures, and Reactivity⋆ (1998)

Wacker, Andreas ; Pritzkow, Hans ; Siebert, Walter

Weinheim : Wiley-Blackwell

Berichte der deutschen chemischen Gesellschaft 1998 (1998), S. 843-849

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ISSN: 1434-1948

Schlagwort(e): Boranes ; Carbenes ; Carbene complexes ; Heterocycles ; Imidazoles ; Chemistry ; General Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: Reactions of the Lewis acids BH3 and BEt3 with trimethylimidazole (1) lead to the borane adducts 2a and 2b. Deprotonation of 2a with n-butyllithium results in the formation of the novel N-borane-substituted imidazol-2-ylidene anion 3a- whereas deprotonated 2b rearranges unexpectedly to the anionic compound 3b-. This can be transformed into the carbene-borane adduct 4 by methylation. The reaction of 3a- with [Mn(CO)5Br] yields the carbene complex 5. Surprisingly, 3a- attacks Fe(CO)5 at a carbon atom which leads to the iron acyl complex anion 6-. The compositions of the products follow from spectroscopic and analytical data and from X-ray structure analyses for Li(thp)+3a-, Li(thf)2+3b- and Li(thp)3+6-.

Materialart: Digitale Medien

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Digitale Medien

Nucleophilic Substitution Reactions with the 3-Borane-1,4,5-trimethylimidazol-2-ylidene Anion. - Unexpected Formation of an Imidazabole Isomer (1999)

Wacker, Andreas ; Pritzkow, Hans ; Siebert, Walter

Weinheim : Wiley-Blackwell

Berichte der deutschen chemischen Gesellschaft 1999 (1999), S. 789-793

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Details

ISSN: 1434-1948

Schlagwort(e): Boranes ; Carbenes ; Heterocycles ; Imidazoles ; X-ray structures ; Chemistry ; General Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: The nucleophilic carbene 3-borane-1,4,5-trimethylimidazol-2-ylidene anion (1-) reacts with the electrophiles CH3I, (CH3)3SiCl, (CH3)3SnCl, and the bromodiazaboroline 7 to form the 2-substituted imidazoles 4, 5, 6, and 8. With triethylborane, the anionic carbene borane adduct 9- is obtained. An unexpected result was achieved when chlorodimethoxyborane and HBCl2 · S(CH3)2 were used as electrophiles. In both cases only the imidazabole 14a could be isolated. Imidazole 5, the imidazole borane adduct 3a and the imidazabole 14a were characterized by X-ray structure analyses.

Zusätzliches Material: 3 Ill.

Materialart: Digitale Medien

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