Date of Award
College of Science, Engineering, and Technology (COSET)
MS in Chemistry
Professor John B. Sapp
The resolution of bis-2-naphthol sulfone is the goal of this research. In a manner similar to that of other resolved diols such as bi-2-naphthol and bis-2-naphthol sulfide, it was proposed that bis-2-naphthol sulfone might also be resolved. By resolving the recemic mixture, the substituted derivatives are generally found in a pure enantiomeric form. The recemic mixture of bis-2-naphthol sulfone can be prepared by combining and stirring bis-2-naphthol sulfide with hydrogen peroxide for 48 hours at room temperature. The original procedure utilized cinchonine salt ofbis-2-naphthol sulfone to resolve the recemic cyclic biphenyl phosphate. Procedures that followed, used commercially available a-methyl phenyl amine. The methods we will attempt to follow include the cyclic amide method and, that of cinchonine salts. There are other procedures that have been used to resolve diols such as partial hydrolysis and inclusion complexes with chiral tartaric acid and with chiral cinchonidium halides. Partial hydrolysis of corresponding esters is a helpful process 111 when trying to resolve enantiomerically pure alcohols. Both of the inclusion complexes have been used to resolve enantiomers similar to those resolves by the cyclic phosphate method. All of the procedures have been successful in resolving enantiomers including the cyclic phosphate method, which will be the focus of our research. IV
Shahid, Khawaja Muhammad, "Resolution of BIS-2-Naphthol Sulfone Via Diastereomeric Phosphates" (2004). Theses (Pre-2016). 94.