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Title:Stereochemical Course of the Tandem [4+2]/[3+2] Cycloaddition of Nitroalkenes
Author(s):Seierstad, Mark Jason
Doctoral Committee Chair(s):Denmark, Scott E.
Department / Program:Chemistry
Discipline:Chemistry
Degree Granting Institution:University of Illinois at Urbana-Champaign
Degree:Ph.D.
Genre:Dissertation
Subject(s):Chemistry, Organic
Abstract:The [4+2] cycloaddition of nitrobutene was further examined with both experimental and theoretical studies. Small, soft Lewis acids (such as Me 3Al) promote endo cycloaddition with the vinyl ether reacting in an s-trans conformation. Most other Lewis acids favor exo cycloaddition due either to their size (such as MAPh) or the conformation they force upon the nitroalkene-Lewis acid complex (such as SnCl4). The s-trans vinyl ether conformation is also favored in these cases, except when phenylcyclohexanol-derived vinyl ethers are used. The s-trans conformation is then disfavored by hard, halogenated Lewis acids (such as SnCl4), and the s-cis conformation is favored.
Issue Date:2000
Type:Text
Language:English
Description:380 p.
Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 2000.
URI:http://hdl.handle.net/2142/84498
Other Identifier(s):(MiAaPQ)AAI9990133
Date Available in IDEALS:2015-09-25
Date Deposited:2000


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