Vinyl ether hydrolysis. XIV. 2-Methoxy-2,3-dihydropyran: concurrent reaction of vinyl ether and acetal functional groups

@inproceedings{Burt1980VinylEH,
  title={Vinyl ether hydrolysis. XIV. 2-Methoxy-2,3-dihydropyran: concurrent reaction of vinyl ether and acetal functional groups},
  author={Ronald A. Burt and Yvonne Chiang and Alexander J. Kresge},
  year={1980}
}
The hydrolysis of 2-methoxy-2,3-dihydropyran shows a normal isotope effect (kH/kD > 1) under catalysis by the hydrogen ion and gives an accurately linear dependence of reaction rate upon undissociated acid concentration in cyanoacetic acid and formic acid buffer solutions. This substrate, therefore, unlike its higher homolog, 9-methoxyoxacyclonon-2-ene, provides no evidence in support of an anything but a normal mechanism for vinyl ether hydrolysis. Analysis of the hydrogen isotope effect… CONTINUE READING