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




Knishevitsky, Arthur V.
Korotkikh, Nikolai I.
Cowley, Alan H.
Moore, Jennifer A.
Vasudevan, Kalyan V.
Pekhtereva, Tatyana M.
Shvaika, Oles P.

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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.



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Knishevitsky, Arthur V., Nikolai I. Korotkikh, Alan H. Cowley, Jennifer A. Moore, Kalyan V. Vasudevan, Tatyana M. Pekhtereva, and Oles P. Shvaika. >A base induced transformation of a 1, 3-dimethyl-1, 3-di-(1-adamantyl) formamidinium salt into β-[methyl-(1-adamantyl) amino] acrylonitriles in aliphatic nitriles.> ARKIVOC, 2 (2012): 60-73.