Benzylation and Related Alkylations of α-Dimethylaminophenylacetonitrile by Means of Alkali Amides. Dehydrocyanation of Products to Form Enamines¹

An Aldimine Cross‐Coupling for the Diastereoselective Synthesis of Unsymmetrical 1,2‐Diamines

“…Only N,N-disubstituted a-aminonitriles can be converted into stable lithium salts, which may be used as acylanion equivalents. [5][6][7][8] In contrast to these and other a-amino-substituted carbanion equivalents, [9] the ketene iminates 2 have the advantage that after their addition to an electrophile, no additional deprotection steps are necessary to liberate the amino function. The cyano group can be removed from the addition products under mild conditions, [10] thus rendering these ketene iminates easily accessible a-amino carbanion equivalents bearing a variable N substituent.…”

Difluoromethylation of some C–H acids with chlorodifluoromethane under conditions of phase transfer catalysis (PTC)

“…Column chromatography was performed on Merck Kieselgel 60 (230-400 mesh) with hexane and ethyl acetate mixtures (gradient) as eluents. Chlorodifluoromethane, nitrile 1a, malonates 1h-k and 9-methylsulfanylfluorene (1o) were commercial, while nitriles 1b [35], 1c [36], 1d [37], 1e [38], 1f [39], 1g [40], (phenyl)ethylcyanoacetate (1l) [41] and desoxybenzoines 1m,n [42] were prepared by literature procedures.…”

An Efficient and Facile Synthesis of Capsaicin‐Like Compounds as Agonists of the TRPV1 Receptor

“…The mixture was cooled on ice prior to the addition of an aqueous solution of NaCN (0.8 g, 0.016 mol). The mixture was stirred at room temperature overnight [21,22] and then extracted with Et 2 O (2× 50 mL). The organic portions were washed with water (20 mL) and evaporated under reduced pressure to give a colourless oil, 2.6 g, 95 % yield.…”