Abstract
The synthesis of several cyclic dialkoxy orthoesters is reported. Acid hydrolysis of these orthoesters under kinetically controlled conditions gives the corresponding hydroxy esters only. Conformationally rigid cyclic mixed orthoesters give a hydroxy ester by exclusive loss of the axial alkoxy group. A cyclic orthoester can have nine different gauche conformations. It is shown that they are hydrolyzed through only one gauche conformer. These results bring further experimental evidence that there is a stereoelectronic control in the cleavage of tetrahedral intermediates in the hydrolysis of esters.
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Disclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.