Abstract
The microenvironment surrounding the active sites in polymer-supported reagents can be tailored for maximized kinetics and yields in organic reactions. Results with the Mitsunobu reaction are presented. Cross-linked copolymers of poly(vinylbenzyl chloride) are substituted with diphenylphosphine ligands at 18, 40, 67, and 100% substitution and used under Mitsunobu conditions to probe benzyl benzoate formation. It is found that the choice of groups surrounding a ligand can be as important as the choice of ligand. Decreasing the percent substitution while increasing the number of unsubstituted phenyl rings directly bonded to the polymer backbone increases the percent alcohol conversion at a 0.1 h contact time (41.7, 68.4, 83.7, and 94.5% conversion for polymers at 100, 67, 40, and 18% substitution). Polymers at 18 and 40% substitution give an equilibrium solution that is purer (97.6 and 97.0% ester) than that with a comparable soluble reagent (85.3% ester). The rapid conversion and high yield obtained as the...
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.
