Stereochemical Course of the Tandem [4+2]/[3+2] Cycloaddition of Nitroalkenes
Seierstad, Mark Jason
This item is only available for download by members of the University of Illinois community. Students, faculty, and staff at the U of I may log in with your NetID and password to view the item. If you are trying to access an Illinois-restricted dissertation or thesis, you can request a copy through your library's Inter-Library Loan office or purchase a copy directly from ProQuest.
Permalink
https://hdl.handle.net/2142/84498
Description
Title
Stereochemical Course of the Tandem [4+2]/[3+2] Cycloaddition of Nitroalkenes
Author(s)
Seierstad, Mark Jason
Issue Date
2000
Doctoral Committee Chair(s)
Denmark, Scott E.
Department of Study
Chemistry
Discipline
Chemistry
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
Ph.D.
Degree Level
Dissertation
Keyword(s)
Chemistry, Organic
Language
eng
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.
Use this login method if you
don't
have an
@illinois.edu
email address.
(Oops, I do have one)
IDEALS migrated to a new platform on June 23, 2022. If you created
your account prior to this date, you will have to reset your password
using the forgot-password link below.
