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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.
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author
; and
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
additional info
The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)
id
2b7d8d4c-3485-492e-b0a5-f6548a5dca1b (old id 33196)
date added to LUP
2016-04-01 16:29:29
date last changed
2022-01-28 20:06:48
@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}},
  doi          = {{10.1016/S0040-4020(97)10390-8}},
  volume       = {{54}},
  year         = {{1998}},
}