Galvanostatic and potentiostatic fluorination of 2-indanone, 1-indanone and 1,3-indandione in Et3N 4HF medium. Adsorption effects on yield and product selectivity
IR@CECRI: CSIR-Central Electrochemical Research Institute, Karaikudi
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| Title |
Galvanostatic and potentiostatic fluorination of 2-indanone, 1-indanone and 1,3-indandione in Et3N 4HF medium. Adsorption effects on yield
and product selectivity
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| Creator |
Ilayaraja, N.
Noel, M. |
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| Subject |
Electroorganic
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| Description |
Selective electrochemical fluorination (SEF) of 1-indanone, 2-indanone and 1,3-indandione were carried
out in Et3N � 4HF ionic liquid. Cyclic voltammetric measurements indicated that the ionic liquid undergoes
oxidation below 2 V on platinum electrode while the background limit is extended up to 2.3 V on
glassy carbon electrode. Well defined voltammetric peaks were observed for all the three compounds
on glassy carbon electrode. Significant absorption effects were also noticed. Preparative electrolysis indicated
lower selectivity for all the three compounds under galvanostatic conditions when compared to
potentiostatic conditions. Both under galvanostatic and potentiostatic conditions, 2-indanone, which
exhibits weak adsorption, gave 1-fluoro-2-indanone with high selectivity. 1-Indanone exhibits higher
anodic oxidation potential around 2 V. 1,3-Indandione exhibited strong intermediate or product adsorption
during voltammetric measurements. The yield and selectivity were much lower for these two compounds
under galvanostatic conditions. Quite interestingly in both these cases, the selectivity close to
70% for the monofluorinated compound could be achieved under potentiostatic conditions by passing
up to 6 F/mole of electric charge. Prevention of formation of over oxidation products under potentiostatic
conditions may be the main cause for this improvement as suggested by chronoamperometric
measurements.
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| Publisher |
Elsevier B.V.
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| Date |
2010
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| Type |
Article
PeerReviewed |
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| Format |
application/pdf
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| Identifier |
http://cecri.csircentral.net/315/1/2010-075.pdf
Ilayaraja, N. and Noel, M. (2010) Galvanostatic and potentiostatic fluorination of 2-indanone, 1-indanone and 1,3-indandione in Et3N 4HF medium. Adsorption effects on yield and product selectivity. Journal of Electroanalytical Chemistry, 638. pp. 39-45. ISSN 1572-6657 |
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| Relation |
http://cecri.csircentral.net/315/
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