Files in this item
Files | Description | Format |
---|---|---|
application/pdf ![]() ![]() | (no description provided) |
Description
Title: | Studies on the Total Synthesis of (+/-)-Cameroonan-7alpha-Ol and Presilphiperfolan-8-Ol and Discovery of a Novel Stereoselective Prins Cyclization of Delta,epsilon-Unsaturated Ketones |
Author(s): | Davis, Chad Eric |
Doctoral Committee Chair(s): | Coates, Robert M. |
Department / Program: | Chemistry |
Discipline: | Chemistry |
Degree Granting Institution: | University of Illinois at Urbana-Champaign |
Degree: | Ph.D. |
Genre: | Dissertation |
Subject(s): | Chemistry, Organic |
Abstract: | A novel stereoselective Prins cyclization reaction of unsaturated ketones was discovered. It was found that reaction of TiCl4 with delta,epsilon- or epsilon,zeta-unsaturated ketones at low temperature followed by buffered methanolysis provided monocyclic and bicyclic cis 3-chlorocyclohexanols. Testing of ten unsaturated ketones and four acid activators provided evidence for substrate generality while the stereoselectivity was rationalized by intramolecular delivery of the nucleophile. |
Issue Date: | 2003 |
Type: | Text |
Language: | English |
Description: | 290 p. Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 2003. |
URI: | http://hdl.handle.net/2142/84098 |
Other Identifier(s): | (MiAaPQ)AAI3086042 |
Date Available in IDEALS: | 2015-09-25 |
Date Deposited: | 2003 |
This item appears in the following Collection(s)
-
Dissertations and Theses - Chemistry
-
Graduate Dissertations and Theses at Illinois
Graduate Theses and Dissertations at Illinois