Details
| Originalsprache | Englisch |
|---|---|
| Seiten (von - bis) | 4903-4914 |
| Seitenumfang | 12 |
| Fachzeitschrift | European Journal of Inorganic Chemistry |
| Jahrgang | 2021 |
| Ausgabenummer | 47 |
| Frühes Online-Datum | 29 Sept. 2021 |
| Publikationsstatus | Veröffentlicht - 16 Dez. 2021 |
Abstract
Ferrocenyl triflates are known to undergo anionic thia-Fries rearrangements at low temperature in high yields. In order to expand the scope of this reaction, ferrocenyl sulfonates and sulfonylferrocenes were prepared and their reactivity investigated. Treatment of ferrocenyl fluorosulfonate with lithium 2,2,6,6-tetramethylpiperidide gave rise to a new anionic thia-Fries rearrangement at ferrocene. The formation of a rare oxathiine was observed with ferrocenyl (pentafluorophenyl)sulfonate as a result of an ortho lithiation and a subsequent intramolecular nucleophilic aromatic substitution. In contrast to fluorinated ferrocenyl sulfonates, fluorosulfonylferrocene as well as (trifluoromethylsulfonyl)ferrocene underwent ortho lithiation under comparable reaction conditions.
ASJC Scopus Sachgebiete
- Chemie (insg.)
- Anorganische Chemie
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in: European Journal of Inorganic Chemistry, Jahrgang 2021, Nr. 47, 16.12.2021, S. 4903-4914.
Publikation: Beitrag in Fachzeitschrift › Artikel › Forschung › Peer-Review
}
TY - JOUR
T1 - Fluorosulfonylferrocene, (Trifluoromethylsulfonyl)ferrocene and New Ferrocenyl Sulfonates
T2 - Directed ortho Lithiation and New Anionic Thia-Fries Rearrangements at Ferrocene
AU - Boston, Geanne M.R.
AU - Philipp, Hendrik M.
AU - Butenschön, Holger
N1 - Funding Information: We thank Dr. Gerald Dräger, Institut für Organische Chemie, Leibniz Universität Hannover, for help with the crystal structure analysis. We acknowledge experimental support by Ms. Jessica Niers and Mr. Henry Struwe. We appreciate a donation of ferrocene by Innospec Deutschland GmbH. Open Access funding enabled and organized by Projekt DEAL.
PY - 2021/12/16
Y1 - 2021/12/16
N2 - Ferrocenyl triflates are known to undergo anionic thia-Fries rearrangements at low temperature in high yields. In order to expand the scope of this reaction, ferrocenyl sulfonates and sulfonylferrocenes were prepared and their reactivity investigated. Treatment of ferrocenyl fluorosulfonate with lithium 2,2,6,6-tetramethylpiperidide gave rise to a new anionic thia-Fries rearrangement at ferrocene. The formation of a rare oxathiine was observed with ferrocenyl (pentafluorophenyl)sulfonate as a result of an ortho lithiation and a subsequent intramolecular nucleophilic aromatic substitution. In contrast to fluorinated ferrocenyl sulfonates, fluorosulfonylferrocene as well as (trifluoromethylsulfonyl)ferrocene underwent ortho lithiation under comparable reaction conditions.
AB - Ferrocenyl triflates are known to undergo anionic thia-Fries rearrangements at low temperature in high yields. In order to expand the scope of this reaction, ferrocenyl sulfonates and sulfonylferrocenes were prepared and their reactivity investigated. Treatment of ferrocenyl fluorosulfonate with lithium 2,2,6,6-tetramethylpiperidide gave rise to a new anionic thia-Fries rearrangement at ferrocene. The formation of a rare oxathiine was observed with ferrocenyl (pentafluorophenyl)sulfonate as a result of an ortho lithiation and a subsequent intramolecular nucleophilic aromatic substitution. In contrast to fluorinated ferrocenyl sulfonates, fluorosulfonylferrocene as well as (trifluoromethylsulfonyl)ferrocene underwent ortho lithiation under comparable reaction conditions.
KW - (Trifluoromethyl)sulfonylferrocene
KW - 1,2-Oxathiin
KW - Anionic thia-Fries rearrangement
KW - Fluorosulfonylferrocene
KW - ortho Lithiation
UR - http://www.scopus.com/inward/record.url?scp=85118574157&partnerID=8YFLogxK
U2 - 10.1002/ejic.202100785
DO - 10.1002/ejic.202100785
M3 - Article
AN - SCOPUS:85118574157
VL - 2021
SP - 4903
EP - 4914
JO - European Journal of Inorganic Chemistry
JF - European Journal of Inorganic Chemistry
SN - 1434-1948
IS - 47
ER -