99967-63-2Relevant academic research and scientific papers
Radical-chain redox rearrangement of cyclic benzylidene acetals to benzoate esters in the presence of thiols
Roberts, Brian P.,Smits, Teika M.
, p. 137 - 140 (2007/10/03)
Cyclic benzylidene acetals derived from 1,2- and 1,3-diols undergo an efficient ring-opening redox rearrangement to give benzoate esters in the presence of a peroxide initiator and a thiol, which acts as a polarity-reversal catalyst to promote the radical-chain reaction.
Substitution of 2-(Sulfonyloxy)carboxylates with Oxygene and Sulfur Nucleophiles without Racemization
Burkard, Ulrike,Effenberger, Franz
, p. 1594 - 1612 (2016/06/15)
The ethyl 2-(sulfonyloxy)propionates (S)-1a-c react with phenolates formed from 2 and with carboxylates 8 to give the respective 2-(aryloxy)- (R)-3 and 2-(acyloxy)propionates (R)-9 with inversion of configuration.Due to the high leaving tendency of the triflate group, (S)-1a generally give higher yields of substitution products under milder conditions than the corresponding mesylate (S)-1b and tosylate (S)-1c.In the case of the reaction of malic and succinic acid derivatives only the triflate (S)-10a is converted to the acyloxy compounds (R)-12 with carboxylates 8 atlow temperature (-45 deg C); with the mesylates 10b and the bromide 10d only elimination is observed.Mercaptides and thiophenolates formed from 17 react with (S)-1a-c analogously.With potassium thiocyanate 1a,b react almost exclusively to give the thiocyanate 19; only traces of the corresponding isothiocyanate 20 are obtained.
