Abstract
The reactions of unsymmetrically substituted ketones with trichloroacetyl p-toluenesulphonate, isopropenyl acetate and acetic anhydride were investigated. Trichloroacetyl p-toluenesulphonate converted the saturated ketone 2 to the enol tosylate 5 but testosterone acetate 6 to the corresponding dienol trichloroacetate 7b. Reaction of the ketones 1,2 and 10 with isopropenyl acetate or acetic anhydride in the presence of acid led to isomeric enol acetates 3,4 and 11. The ratio of the isomeric enol acetates differed according to the acid used, when isopropenyl acetate was employed, but was independent of the acid, when acetic anhydride was used. It is suggested that the formation of enol acetates involves addition of either acetic anhydride (when acetic anhydride is used) or mixed anhydride (when isopropenyl acetate or the mixed anhydride is used) to give a gem disubstituted intermediate.
Published Version
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: 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.
