Date of Award
Doctor of Philosophy
Richard C. Larock
John G. Verkade
2,3-Disubstituted benzo[b]selenophenes have been prepared by the electrophilic cyclization of various 1-(1-alkynyl)-2-(methylseleno)arenes by Br2, NBS, I2, ICl, PhSeCl, PhSeBr and Hg(OAc) 2. This method tolerates a wide variety of functional groups, including alcohol, ester, nitrile, nitro and silyl groups, and proceeds under exceptionally mild reaction conditions. A cationic intermediate in the cyclization with Br2 has been isolated and studied, providing evidence for a stepwise cyclization process.
Digital Repository @ Iowa State University, http://lib.dr.iastate.edu/
Kesharwani, Tanay, "Studies in electrophilic cyclization, palladium migration and cationic polymerization" (2008). Retrospective Theses and Dissertations. 15754.