Browsing by Subject "biscarbenes"

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A Base Induced Transformation Of A 1,3-Dimethyl-1,3-Di-(1-Adamantyl)Formamidinium Salt Into Beta- Methyl-(1-Adamantyl)Amino Acrylonitriles In Aliphatic Nitriles
(2012) Knishevitsky, Arthur V.; Korotkikh, Nikolai I.; Cowley, Alan H.; Moore, Jennifer A.; Vasudevan, Kalyan V.; Pekhtereva, Tatyana M.; Shvaika, Oles P.; Cowley, Alan H.; Moore, Jennifer A.; Vasudevan, Kalyan V.
A novel 1,3-dimethyl-1,3-di-(1-adamantyl)formamidinium perchlorate has been prepared via the Vilsmeier-Haack reaction of N-methyl-N-(1-adamantyl)formamide and N-methyl-N-(1-adamantyl) amine in a mixture of phosphorus oxychloride and benzene. The new formamidinium salt was found to undergo addition-elimination reactions when treated with sodium hydride in acetonitrile or propionitrile solution, thereby forming the corresponding beta-[methyl(1-adamantyl)amino]acrylonitriles and N-methyl-N-(1-adamantyl) amine. The H-1 and C-13 NMR spectra and the single-crystal X-ray structure of the new formamidinium salt have been determined along with those of the related compound 1,3-di-(1-adamantyl)-1-cyanoamidine and the corresponding beta-(dialkylamino)acrylonitriles.
Review: Stable Heteroaromatic Carbenes Of The Benzimidazole And 1,2,4-Triazole Series
(2005) Korotkikh, Nikolai I.; Shvaika, Oles P.; Rayenko, Gennady F.; Kiselyov, Artyom V.; Knishevitsky, Arthur V.; Cowley, Alan H.; Jones, Jamie N.; Macdonald, Charles L. B.; Cowley, Alan H.; Jones, Jamie N.; Macdonald, Charles L. B.
The review is focused on new data concerning the syntheses and selected properties of stable heteroaromatic monocarbenes of the benzimidazole and 1,2,4-triazole series, biscarbenes, anionocarbenes of the 1,2,4-triazole series, and cryptocarbenes. The syntheses of the precursors to these compounds are also described. Special attention is paid to C-H insertion reactions, X-ray structural data and spectral characteristics of the carbenes and their analogues.
Syntheses of Sterically Shielded Stable Carbenes of the 1,2,4-Triazole Series and their Corresponding Palladium Complexes: Efficient Catalysts for Chloroarene Hydrodechlorination
(2014-11) Glinyanay, Nataliya V.; Saberov, Vagiz S.; Korotkikh, Nikolai I.; Cowley, Alan H.; Butorac, Rachel R.; Evans, Daniel A.; Pekhtereva, Tatyana M.; Popov, Anatolii F.; Shvaika, Oles P.; Cowley, Alan H.; Butorac, Rachel R.; Evans, Daniel A.
The new sterically shielded 1,3,4-trisubstituted 1,2,4-triazol-5-ylidenes 8b-d were synthesized by a three step method starting from 2-phenyl-1,3,4-oxadiazole. The syntheses of palladium complexes 9a-d and 10a-d (including the sterically shielded derivatives 9c,d and 10a-d) were carried out via the reactions of the stable carbenes 8a-d with palladium halogenide salts in THF or toluene solution. Complexes 9c,d and 10a-d were found to be excellent catalysts for the reductive dechlorination (hydrodechlorination) of p-dichlorobenzene. The structures of 8c, 9a,b, and 10a were determined by single-crystal X-ray diffraction.
Synthesis Of Heteroaromatic 3,3 '-Bridged Biscarbenes Of The 1,2,4-Triazole Series And Their Properties
(2008) Kiselyov, Artyom V.; Korotkikh, Nikolai I.; Cowley, Alan H.; Moore, Jennifer A.; Findlater, Michael A.; Pekhtereva, Tatyana M.; Shvaika, Oles P.; Cowley, Alan H.; Moore, Jennifer A.; Findlater, Michael A.
The stable 3,3'-bridged biscarbenes, 1,4- and 1,3-bis[1-alkyl-4-phenyl-1,2,4-triazol-5-yliden-3yl] benzenes (5a,b,d) and 1,3-bis[1-(1-adamantyl)-4-phenyl-1,2,4-triazol-5-yliden-3-yl] butane (5c) have been prepared. Treatment of 5b with copper (I) chloride in tetrahydrofuran/acetonitrile solution and cobalt (II) chloride in acetonitrile or acetonitrile/toluene solution afforded the biscarbene copper (I) complex 8. The reactions of 5d with diphenyldiazomethane and sulfur resulted in the novel bisthione 6 and bisazine (7) derivatives, respectively. The X-ray crystal structures of 5d, 8 were determined.