Degree Type

Dissertation

Date of Award

2008

Degree Name

Doctor of Philosophy

Department

Chemistry

First Advisor

Richard C. Larock

Second Advisor

Walter Trahanovsky

Third Advisor

John G. Verkade

Abstract

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.

DOI

https://doi.org/10.31274/rtd-180813-16959

Publisher

Digital Repository @ Iowa State University, http://lib.dr.iastate.edu/

Copyright Owner

Tanay Kesharwani

Language

en

Proquest ID

AAI3330842

OCLC Number

601376145

ISBN

9780549871767

File Format

application/pdf

File Size

318 pages

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