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

Forskningsoutput: TidskriftsbidragArtikel i vetenskaplig tidskrift

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.

Detaljer

Författare
  • Anders Tsirk
  • Salo Gronowitz
  • Anna-Britta Hörnfeldt
Forskningsområden

Ämnesklassifikation (UKÄ) – OBLIGATORISK

  • Organisk kemi
Originalspråkengelska
Sidor (från-till)1817-1834
TidskriftTetrahedron
Volym54
Utgåva nummer9
StatusPublished - 1998
PublikationskategoriForskning
Peer review utfördJa
Externt publiceradJa

Relaterad forskningsoutput

Anders Sebastian Tsirk, 1997, 179 s.

Forskningsoutput: AvhandlingDoktorsavhandling (sammanläggning)

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