41309-99-3

Upstream product

• 7677-24-9 trimethylsilyl cyanide 
• 75-36-5 acetyl chloride 
• 108-98-5 thiophenol 

Downstream Products

• 87712-90-1 (S,S)-(-)-α-<(1-phenylethyl)amino>-α-propionitrile hydrochloride 
• 87712-89-8 (R,R)-(+)-α-<(1-phenylethyl)amino>-α-propionitrile hydrochloride 
• 96825-24-0 (S)-2-((R)-1-Phenyl-ethylamino)-propionitrile; hydrochloride 
• 21053-95-2 γ-methyl-α-phenyltetronic acid 
• 62763-33-1 (+/-)-3-hydroxy-1-phenyl-2-butanone 
• 210710-50-2 3-amino-6-phenyl-hexan-2-ol 
• 78-97-7 2-hydroxy-propionitrile 

Relevant academic research and scientific papers

ZnI2-catalyzed cyanation of acyl chlorides with TMS-CN: An interesting role of iodine

Both aliphatic and aromatic acyl cyanides have been synthesized with TMSCN and acyl chloride with ZnI2 (0.5 mol%). However the in situ generated I2 is proposed accounting for the formation of by-product O-TMS enolate at high catalyst loading rather than 0.5 mol%. Asymmetric reduction of benzoyl cyanide with borane has been explored in 82% yield and 24% ee.

Thermolysis of acylazo O-trimethylsilyl cyanohydrins: Azoalkanes yielding captodatively substituted radicals

A new synthetic method has been developed for preparing azoalkanes bearing geminal α-cyano and α-trimethylsiloxy groups. While the symmetrical compound 5 decomposes near room temperature to afford, almost entirely, the C-C dimers, the unsymmetrical azoalkane 3 requires heating to 75 °C. The thermolysis activation parameters of 3 and 5 can be rationalized on steric grounds without invoking captodative radical stabilization. A 13C NMR product study of photolyzed 3 in the presence of TEMPO at 21 °C shows that the fate of caged [tert-butyl, 1-trimethylsiloxy-1-cyanoethyl (14)] radical pairs is disproportionation, 17%, cage recombination, 20%, and cage escape, 63%.