Date of Award
Program or Major
Master of Science
The Synthesis of Dibenzo anthracenes 3, 7-diphenyldibenzo[a,h] anthracene (1) and 3,6-diphenyl-9-methoxydibenzo [a,j] anthracene ( 2) as well as a phenyl substituted picene (3) was attempted utilizing an original, generic, scheme. An Umpolung reaction between a 1,3-dithiane and a variety of dibromomethyl benzene hubs was performed to generate the carbon framework of 1, 2 and 3. Deprotection of the thioacetal groups yielded a carbonyl product which upon Grignard addition and dehydration could potentially be converted to the desired product. The proposed synthetic design allows for a variety of substitution patterns about the parent PAHs, without adding synthetic steps.
Dunn, Joseph M., "A versatile synthetic approach towards the synthesis of new polycyclic aromatic hydrocarbons using Scholl, Grignard and Umpolung chemistries" (2010). Master's Theses and Capstones. 561.