Multivariate Optimization and Mechanistic Considerations of the Amine Induced Ring-Opening Reaction of 2-Alkyl-3-bromo-5-methylthiophene-1,1-dioxides
(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:
https://lup.lub.lu.se/record/33196
- author
- Tsirk, Anders ; Gronowitz, Salo and Hörnfeldt, Anna-Britta
- publishing date
- 1998
- 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}}, }