34147-85-8Relevant academic research and scientific papers
Synergistic effect in the catalysis by pyridine N-oxide-triethylamine mixture of acyl transfer processes with participation of benzoyl, diethoxyphosphinoyl, and p-toluenesulfonyl chlorides
Belousova,Savelova,Simanenko,Panchenko
, p. 111 - 114 (2002)
The kinetics of benzoylation of substituted phenols with benzoyl chloride in the presence of pyridine N-oxide-triethylamine was analyzed with regard to previously reported data on benzoylation, phosphorylation, and sulfonylation of phenols and carboxylic acids. A common mechanism of the synergistic effect was established. The synergistic effect decreases in the series PhCOCl (EtO)2POCl > TsCl.
Unusual Reaction of Azoxybenzenes with p-Toluenesulfonic Acid in Acetic Anhydride
Shimao, Ichiro,Fujimori, Ken,Oae, Shigeru
, p. 1538 - 1542 (2007/10/02)
Treatment of azoxybenzene with p-toluenesulfonic acid in acetic anhydride gave tosylates of 4- and 2-(phenylazo)phenols, and the corresponding acetates as by-product, besides azobenzene.However, a similar reaction of 4,4'-difluoroazoxybenzene gave 2-tosyloxy-4,4'-difluoroazobenzene as rearrangement product, besides 4-fluorophenyl tosylate and 4-fluorophenyl acetate.Meanwhile, the reaction of 4,4'-diacetoxyazoxybenzene afforded 4-acetoxyphenyl tosylate and hydroquinone diacetate in high yields.These unique reactions involve C-N bond cleavage, and may proceed through a pathway involving formation of benzenediazonium ion as the key intermediate.
