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NEW ORGANIC TRANSFORMATIONS BASED ON ELECTROPHILIC AND
SUPERELECTROPHILIC ACTIVATION IN STRONG ACIDS
by
Farzaneh Paknia
A Dissertation Presented to the
FACULTY OF THE GRADUATE SCHOOL
UNIVERSITY OF SOUTHERN CALIFORNIA
In Partial Fulfillment of the
Requirements for the Degree
DOCTOR OF PHILOSOPHY
(CHEMISTRY)
August 2008
Copyright 2008 Farzaneh Paknia
Object Description
| Title | New organic transformations based on electrophilic and superelectrophilic activation in strong acids |
| Author | Paknia, Farzaneh |
| Author email | paknia@usc.edu |
| Degree | Doctor of Philosophy |
| Document type | Dissertation |
| Degree program | Chemistry |
| School | College of Letters, Arts and Sciences |
| Date defended/completed | 2008-06-25 |
| Date submitted | 2008 |
| Restricted until | Restricted until 24 July 2010. |
| Date published | 2010-07-24 |
| Advisor (committee chair) | Prakash, Surya |
| Advisor (committee member) |
Olah, Geroge Petruska, John |
| Abstract | This dissertation covers the development of new methodologies based on Friedel-Crafts alkylation, acylation and hydroxyalkylation through electrophilic or superelectrophilic activation using boron trifluoride monohydrate and polymer supported superacids for the synthesis of fluorinated and heterocyclic compounds.; Chapter 1 briefly reviews the history of superelectrophiles and their chemistry. Superelectrophilic chemistry has made a significant contribution in Friedel-Crafts and related electrophilic reactions.; Chapter 2 deals with the triflic acid catalyzed Friedel-Crafts alkylation reaction of trifluoromethylated acrylic acid with arenes for the synthesis of biologically important trifluoromethylated dihydrocoumarins, indanones and arylpropanoic acids.; Chapter 3 explores the application of BF3-H2O as an efficient acid catalyst as well as a solvent for Friedel-Crafts hydroxyalkylation reaction of trifluoromethylated and difluoromethylated hemiacetals with aromatics for the synthesis of trifluoroethylated and difluoroethylated aromatic building blocks.; Chapter 4 describes the application of BF3-H2O as a substitute to trifluoromethanesulfonic acid for hydroxyalkylation reaction of pyridinecarboxaldehydes with aromatics through superelectrophilic protosolvation. Preparation of various biologically important diarylmethylpyridine derivatives has been discussed.; Chapter 5 encompasses the preparation of poly(4-vinylpyridinium) poly(triflic acid) as a polymer supported (immobilized) solid equivalent of triflic acid. (PVP-TfOH) has been applied as a convenient and efficient solid superacid catalyst for Friedel-Crafts hydroxyalkylation and acylation reactions of arenes through superelectrophilic activation. |
| Keyword | Friedel-Crafts hydroxyalkylation; superacids; superelectrophilic activation |
| Language | English |
| Part of collection | University of Southern California dissertations and theses |
| Publisher (of the original version) | University of Southern California |
| Place of publication (of the original version) | Los Angeles, California |
| Publisher (of the digital version) | University of Southern California. Libraries |
| Type | texts |
| Legacy record ID | usctheses-m1389 |
| Rights | Paknia, Farzaneh |
| Repository name | Libraries, University of Southern California |
| Repository address | Los Angeles, California |
| Repository email | http://www.usc.edu/isd/libraries/services/ask_a_librarian/email/ |
| Filename | etd-Paknia-20080724 |
| Archival file | uscthesesreloadpub_Volume17/etd-Paknia-20080724.pdf |
Description
| Title | Page 1 |
| Full text | NEW ORGANIC TRANSFORMATIONS BASED ON ELECTROPHILIC AND SUPERELECTROPHILIC ACTIVATION IN STRONG ACIDS by Farzaneh Paknia A Dissertation Presented to the FACULTY OF THE GRADUATE SCHOOL UNIVERSITY OF SOUTHERN CALIFORNIA In Partial Fulfillment of the Requirements for the Degree DOCTOR OF PHILOSOPHY (CHEMISTRY) August 2008 Copyright 2008 Farzaneh Paknia |
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