17797-87-4Relevant academic research and scientific papers
Anodic Oxidation of Di-tert-butyl Disulfide: a Facile Method for the Preparation of N-tert-Butylamides
Elothmani, Driss,Do, Quang Tho,Simonet, Jacques,Guillanton, Georges Le
, p. 715 - 717 (1993)
The electrochemical oxidation of di-tert-butyl disulfide is shown to correspond to a one electron process; at 1.3 V, one carbon-sulfur bond is cleaved yielding two intermediate species; the tert-butyl cation and the radical t-BuS-S; a Ritter reaction occurs with the cation when the solvent is a nitrile and the cation dimerizes into a tetrasulfide; at a more positive potential (1.9 V) the two carbon-sulfur bonds are cleaved giving t-Bu cation and sulfur.
Nucleophilic substitution accompanying carbon-carbon bond cleavage assisted by a nitro group
Nakaike, Yumi,Taba, Noriko,Itoh, Shinobu,Tobe, Yoshito,Nishiwaki, Nagatoshi,Ariga, Masahiro
experimental part, p. 2413 - 2417 (2009/09/08)
A 2-nitrated 3-oxoester reacted with amines or alcohols to afford unsymmetrical malonic acid derivatives as a result of nucleophilic substitution accompanying C-C bond cleavage. The 2-nitrated 3-oxoester easily formed ammonium salts with amines. When the amine is liberated from the salt under equilibrium, nucleophilic amine and electrophilic keto ester locate close to each other. This intimate pair effect causes a pseudo intramolecular reaction to occur, giving rise to effective substitution under mild conditions.
Transacylation of α-Aryl-β-keto Esters
Nishiwaki, Nagatoshi,Nishida, Daisei,Ohnishi, Tetsuya,Hidaka, Fumie,Shimizu, Satoru,Tamura, Mina,Hori, Kazushige,Tohda, Yasuo,Ariga, Masahiro
, p. 8650 - 8656 (2007/10/03)
The acyl group of an α-aryl-β-keto ester was readily transferred to N-, O-, and S-nucleophiles. The transacylation from arylated diethyl 3-oxoglutarate to amines led to unsymmetrical malonic acid amide esters in high yields. The present reaction proceeded under mild conditions without formation of detectable byproducts. Only simple experimental manipulations were required. This reaction was also found to be sensitive to steric factors, which enabled the chemoselective monoacylation of diamines and amino alcohols without any modifications such as protection.
