Eine einfache, selektive Synthese von (Z)-tert-Butylketen-O,N-acetalen durch Phenol/Azol-Austauschreaktion
Melting the ketene O,O-acetals 1 with azoles in the presence of a catalytic amount of a proton acid yields the ketene O,N-acetals 2.The products of this phenol-azol substitution reaction are obtained as their (E/Z)-mixtures with the (Z)-isomers highly pre
A Facile Synthesis of Ketene O,N-Acetals and Ketene O,O-Acetals by Tosylate Elimination
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".
Reuther, Wolfgang,Ruland, Alfred,Baus, Ulf
p. 235 - 240
(2007/10/02)
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