One-pot synthesis of anthracene and triarylmethane derivatives catalyzed by BF3:H2O

CHED 312

G. K. Surya Prakash, gprakash@usc.edu, Eric Shah, Chiradeep Panja, Thomas Mathew, Anton Shakhmin, and George A. Olah, olah@usc.edu. Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, Los Angeles, CA 90089-1661
Anthracene derivatives are widely used in organic LED devices, emerging e-paper technology, dyes and in tumor proliferation inhibitors. We explored the synthetic utility of BF3:H2O as a potential alternative to more expensive strong acid systems, which are able to carry out further protonation and effective protosolvation of various electrophiles. In BF3:H2O aromatic aldehydes undergo condensation reaction with aromatics, through hydroxyalkylation to yield polyaryl systems in high yileds. Anthracenes were produced in high yields from 1,2-dicarboxaldehydes via an intramolecular cyclization pathway. Other dicarboxaldehydes (1,3- and 1,4-) gave the corresponding triarylcarboxaldehydes in good yields. These reactions provide an economic and efficient method of producing the industrially important anthracenes and triarylmethanes.

 

Undergraduate Research Poster Session: Organic Chemistry
2:30 PM-4:30 PM, Monday, 11 September 2006 Moscone Center -- Hall D, Poster

Division of Chemical Education

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006