91658-47-8Relevant academic research and scientific papers
ELECTROGENERATED ACID AS AN EFFICIENT CATALYST FOR CYANATION OF ACETALS WITH TRIMETHYLSILYL CYANIDE
Torii, Sigeru,Inokuchi, Tsutomu,Kobayashi, Tohru
, p. 897 - 898 (1984)
A facile cyanation of acetals with trimethylsilyl cyanide, giving the corresponding α-alkoxyalkanenitriles, is achieved by using an electrogenerated acid as an acid-catalyst.
Electrogenerated Acid-Catalyzed Reactions of Acetals, Aldehydes, and Ketones with Organosilicon Compounds, Leading to Aldol Reactions, Allylations, Cyanations, and Hydride Additions
Torii, Sigeru,Inokuchi, Tsutomu,Takagishi, Sadahito,Horike, Hirofumi,Kuroda, Hideki,Uneyama, Kenji
, p. 2173 - 2188 (2007/10/02)
Exquisite use of electrogenerated acid (EG acid) in the silicon-mediated acid-catalyzed reactions; e.g., aldol reactions, allylations, cyanations, and hydride additions is described.The aldol reaction of acetals 1 with enol trimethylsilyl ethers 3 and 1,2-bis(trimethylsiloxy)alkenes 4 gives the corresponding adducts 5 and 6, respectively.The reaction proceeds smoothly with EG acid derived from perchlorate salts such as LiClO4, n-Bu4NClO4, and Mg(ClO4)2 in dichloromethane using platinum electrodes.The amount of electricity required to complete the reaction implies a cationic process which is mediated by the trimethylsilyl moiety.This aldol reaction is further developed with unprotected carbonyl compounds 2 with 3, giving the trimethylsilyl ethers of the adducts 7.Further utility of this EG acid as a catalyst for a chain reaction is exemplified by the successful application in the following conversions: (1) The allylation of acetals 1 with allyltrimethylsilane (8) to give 9, (2) the cyanation of acetals 1 and unmasked 2 with trimethylsilyl cyanide (10) to give 11, 12, and 13, and (3) the hydride addition of acetals 1 with triethylsilane (14) to give 15.
