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Multivariate Optimization and Mechanistic Considerations of the Amine Induced Ring-Opening Reaction of 2-Alkyl-3-bromo-5-methylthiophene-1,1-dioxides

Tsirk, Anders; Gronowitz, Salo and Hörnfeldt, Anna-Britta (1998) In Tetrahedron 54(9). p.1817-1834
Abstract
In the optimization of the ring-opening reaction of thiophene-1,1-dioxides, 3-bromo-2,5-dimethylthiophene-1,1-dioxide (1) and 2-(2-hydroxyethyl)piperidine (7) were chosen as model reagents. Solvent, temperature, molar ratio between amine and dioxide and the amount of solvent were variables included in the optimization. A central composite design was chosen for the investigation and a canonical analysis of the response sur face was performed. When reacting 3-bromo-2-isopropyl-5-trideuteriomethylthiophene-1,1-dioxide (23) with 7 a primary kinetic isotope effect, diminished by internal return, was found for the initial proton abstractions as well as an intramolecular deuterium transfer in the tautomerization of 23.
Please use this url to cite or link to this publication:
author
publishing date
type
Contribution to journal
publication status
published
subject
in
Tetrahedron
volume
54
issue
9
pages
1817 - 1834
publisher
Elsevier
external identifiers
  • scopus:0032567943
ISSN
0040-4020
DOI
10.1016/S0040-4020(97)10390-8
language
English
LU publication?
no
id
2b7d8d4c-3485-492e-b0a5-f6548a5dca1b (old id 33196)
date added to LUP
2007-06-19 14:36:49
date last changed
2017-01-01 07:06:45
@article{2b7d8d4c-3485-492e-b0a5-f6548a5dca1b,
  abstract     = {In the optimization of the ring-opening reaction of thiophene-1,1-dioxides, 3-bromo-2,5-dimethylthiophene-1,1-dioxide (1) and 2-(2-hydroxyethyl)piperidine (7) were chosen as model reagents. Solvent, temperature, molar ratio between amine and dioxide and the amount of solvent were variables included in the optimization. A central composite design was chosen for the investigation and a canonical analysis of the response sur face was performed. When reacting 3-bromo-2-isopropyl-5-trideuteriomethylthiophene-1,1-dioxide (23) with 7 a primary kinetic isotope effect, diminished by internal return, was found for the initial proton abstractions as well as an intramolecular deuterium transfer in the tautomerization of 23.},
  author       = {Tsirk, Anders and Gronowitz, Salo and Hörnfeldt, Anna-Britta},
  issn         = {0040-4020},
  language     = {eng},
  number       = {9},
  pages        = {1817--1834},
  publisher    = {Elsevier},
  series       = {Tetrahedron},
  title        = {Multivariate Optimization and Mechanistic Considerations of the Amine Induced Ring-Opening Reaction of 2-Alkyl-3-bromo-5-methylthiophene-1,1-dioxides},
  url          = {http://dx.doi.org/10.1016/S0040-4020(97)10390-8},
  volume       = {54},
  year         = {1998},
}