Di(1 H,1 H,2 H,2 H-perfluorooctyl)-dibenzo-18-crown-6: A “light fluorous” recyclable phase transfer catalyst

• Published in: Journal of fluorine chemistry Vol. 131; no. 11; pp. 1133 - 1143
• Main Authors: Gourdet, Benoit, Singh, Kuldip, Stuart, Alison M., Vidal, José A.
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 01-11-2010
• Subjects: Aliphatic compounds; Catalysts; Crown ethers; Derivatives; Ethers; Fluorous; Nucleophilic substitution; Parents; Phase transfer catalysts; Recycled; X-rays; Fluorous; Nucleophilic substitution; Crown ethers; Phase transfer catalysts
• ISSN: 0022-1139; 1873-3328
• DOI: 10.1016/j.jfluchem.2010.06.002

The “light fluorous” crown ether can be recycled efficiently by fluorous solid-phase extraction and it gives better PTC catalytic activity than dibenzo-18-crown-6 in aliphatic and aromatic nucleophilic substitutions.
A series of dibenzo-18-crown-6 lariat ethers containing two C
7H
15 (
11), (CH
2)
2C
6F
13 (
14), (CH
2)
2C
8F
17 (
15), NHC
7H
15 (
18) and NHCH
2C
6F
13 (
19) sidearms were prepared and the single crystal X-ray structure of
cis-4,4′-di(1
H,1
H,2
H,2
H-perfluorodecyl)-dibenzo-18-crown-6 (
15a) is reported. The “light fluorous” dibenzo-18-crown-6 ether (
14) has emerged as a stable and robust PTC catalyst, which can be recycled efficiently by fluorous solid-phase extraction, and gives better PTC catalytic activity compared to the parent, non-fluorinated PTC catalyst, dibenzo-18-crown-6, and the alkylated derivative (
11) in aliphatic and aromatic nucleophilic substitutions.