91171-23-2Relevant academic research and scientific papers
A Facile Synthesis of Ketene O,N-Acetals and Ketene O,O-Acetals by Tosylate Elimination
Reuther, Wolfgang,Ruland, Alfred,Baus, Ulf
, p. 235 - 240 (2007/10/02)
Reaction of the alcohols 4 and 5 with p-toluensulfonyl chloride leads to the sulfonic esters 6 and 7, respectively, which on treatment with potassium tert-butylate easily react to give the ketene O,N-acetals 8 and O,O-acetals 9, respectively.The (E/Z) isomers 8 arising from the elimination reaction of 7 were identified by their 1H-NMR data after X-ray analysis of one of the isomers of 8e.On one example it is shown that the elimination reaction proceeds stereoselectively "anti".
