Abstract
A single ethylthio group of diethyl dithioacetals is substituted by acetoxy when dissolved in solutions of acetic acid and acetic anhydride which contain a mercuric salt or a catalytic amount of a strong acid. The substitution is stereoselective as dithioacetals with an asymmetric carbon adjacent to the site of substitution give unequal amounts of diastereomers. Substitution under conditions (with mercuric acetate) under which the diastereomers are stable yields products with a larger percentage of one diastereomer than under conditions (with strong acids) which catalyse epimerization of the monothioacetal products. The same isomer of each pair is the major product when prepared by different synthetic methods.
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.
