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8.2.5.2.1.1 Variation 1: Monoanions

DOI: 10.1055/sos-SD-008-00922

Jonczyk, A.; Kowalkowska, A.Science of Synthesis, (200681142.

Aliphatic nitriles, including acetonitrile, can be deprotonated or alkylated by using sodium amide.[‌9‌‌11‌] Nitriles possessing more than one acidic hydrogen are susceptible to polyalkylation,[‌9‌‌12‌] particularly when the introduced group increases the acidity of the product.[‌13‌] Acetonitrile and other aliphatic nitriles can be exhaustively alkylated by treatment with an excess of sodium amide and an alkylating reagent.[‌9‌‌11‌] Sodium amide can also be used in the alkylation of aliphatic N,N-dimethylcarboxamides or N-methylpyrrolidin-2-one.[‌14‌]

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Me M MM8e-Me MeM eee MM8, Me8M, 8e 88 [‌88‌]
Me Me MM8Me MeMe eee MM8, Me8M, 8e 88 [‌88‌]
8-MeM8M8 M MM8Me MeMe eee MM8, Me8M, 8e 88 [‌88‌]
Me M MM8Me Me(MM8)8Me eee MM8, Me8M, 8e 8888 [‌88‌]

Meeeee eeeee eee eeee ee eeee ee eeeee eee eee Meeeeee eeeeeeeeeeee ee eeeeee[‌88‌,‌88‌] ee eeeeee[‌88‌] ee α-eeeeeeeeeeeeee eeeee (eee eee eee eeeeeeeeeeeee eeeeeeee ee α-eeeeeeeeeeeeee[‌88‌]). Me eee eeee ee eeee ee Meeeeeeee[‌88‌,‌88‌] eee MeeeeeMeeeeee[‌88‌] eeeeeeeeeeeee; ee eeeeeeeee ee eeeeee eeee eeeeeeee[‌88‌,‌88‌] ee, eeeeeeeeeeee, eeeeee[‌88‌] ee eeeeeeeee ee eeeeeee; eee ee eee eeeeeeeee ee eeeeeeee,[‌88‌,‌88‌] eeee ee eee eeeeeeeee ee eeeee eeeeee 8 eeee eeeeeeee 8 (Meeeee 8).[‌88‌]

Meeeee 8 Meeeeeeee ee Meeeeeee[‌88‌]

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Mee eeeeee eeeeee ee 8- eee 8-eeeeeeeeeeeeeeeeee[‌88‌] eee 8- eee 8-eeeee eeeeee eeeeeeee[‌88‌] eee eeeeeeeeeeee eeeeeeeee ee eeeeee eeeeeeeeeeeee ee eeeeee eeeee ee, eee eeeeeee, ee eee eeeeeeeeee ee eeeeeee eeeeeeeeeee 8 eeee eee eeeeeeeee eeeeeeeeeee 8 (Meeeee 8).

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Mee 8-eeeeee eeeee ee 8,8-eeeeeeeeeeeeeeee, 8,8,8-eeeeeeeeeeeeeeeee, ee 8,8-eeeeeeeeeeeeeeeee eeeeeeeee eeeeeeeeee eee eeeeeeeeeeeeeeeee eeee eeeeeee eeee eeeeee eeeee ee eeeeee eeeeeee,[‌88‌,‌88‌] eeeeeee ee ee eee 8-eeeeee eeeee eeee eeeeeeeee eeeeeeee ee eee eeeeeeee ee eeeeeeeeeeee.[‌88‌] Mee eeeeeeeeee ee eeeee eeeeee eeeeeee eeee eeeeeeeeeeeee ee eee eeeeeeee ee 8,8-eeeeeeeeeeeeeee-eeeeeeeee eeeeee eeeee eeeee eeeeee 8-eeeeeeeeeeeeeee eeeeeeee ee eeee eeeeee.[‌88‌]

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Meeeeeee eeeeee eee eeee ee eeeeee ee eee eeeeeeee ee eeeeee eeeee (e.e., ee eee eeeeeeeeeee ee 8-eeeeee-8M-eeeeee eeee eeeeee eee eeeeeeeeeee[‌88‌] ee ee eeeeeeeeeeeeee eeee eeeeeeeeeeeeee eee eeeeeeeeeeeeeeeeeeeee).[‌88‌] Meeeee eeeee eeee eeeeeeee eee eeeeeeee ee eeee eeeeeeeeee eee eeeeeeeeeeee ee eeeeeeeeee, eeeeeeee eeeeeeeeeeeeeeeeee eee eeeeeeeeeeeeeeeeeee eeeeeeee eee eeee eeeeeeeeeee.[‌88‌]

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Meeee 8,8-Meeeeeeeeeeeeeeee [8, M8=Me; M8=M; M8=(MM8)8Me; MMM=MM8Me]:[‌88‌]

Meeeeeeee eeee (Meeeee; Meeeee; Meeeee, Meeeeee Meeeeeeee, Meeeeeeeee Meeeee M), Meeeeeeee (8888), e888, eeee eeeeeeeeee eeee Meee Meeee&Meee, Mee.

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8-Mee-8-eeeeeeeeeeeeeeeeeeee (8, M8=M; M8=Me):[‌88‌]

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M eeee ee MeMM (88.8e, 888eeee) ee ee eeeee eeeeee ee eeeee Me8M eee eeeee eeeeee 8eee ee e eeeeeee eeeeeeeeee ee MeMM8 (888eeee) ee eee MM8 (888eM). Meeee 8eee, e eeee ee MeMMe (88e, 888eeee) ee ee eeeee eeeeee ee Me8M eee eeeee ee eeeeeee ee eeeeeeee (eeeee 8eee), eee eee eeeeeee eee eeeeeee eee 8e. Me eee eeeeeee eeeeee eee eeeeeee, eeee Me8M eee eeeee ee eeeeeeeeee eeeeeeee. Mee MM8 eee eeeeeee eeeeeee (eeeee 88eee) ee e eeeee eeee ee Me8M eee eeeee ee eeeeeeee eee eeeeee ee eeeeeeeeeeeee 888eM. Mee eeeeeee eee eeee eeeeeeeeee eeeeee eeee eeeeeeee eeee eeeeeee eee (888e), eee eeeeee eeee eeeeeeeee, eee eee eeee eeeeeee eeee eee eeeeeeee eeee eeeeeee eeeeeee Meeee Meeee Meeee-Mee ee eeeeee eeeeeee eeeeeeeee eeeeeeeee. Mee Meeee-Mee eee eeeeee eeee e eeeee eeeeee ee eee eeeee eee eee eeeeeeee eeeeeeee eeee eeeeeeeee eeee eee-eeee 8M ee MMe. Mee eeeeeeeee eeeeeee eee eeeeeeeee eeee Me8M (8×) eee eee eeeeeeee eeee eeeeee eeee ee MeMMM8 eee eeeee (MeMM8). Mee eeeeeee eee eeeeeee, eee eee eeeeeee eee eeeeeeeeeeee (Me8M); eeeee: 88e (88%); ee 8888°M.

References


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