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In conclusion, Solkaneꢀ 365mfc is introduced as a novel and
Prakash, M. Mandal, S. Schweizer, N. A. Petasis and G. A. Olah,
J. Org. Chem., 2002, 67, 3718; (j) G. Mloston, G. K. S. Prakash,
G. A. Olah and H. Heimgartner, Helv. Chim. Acta, 2002, 85, 1644;
(k) G. K. S. Prakash, M. Mandal, C. Panja, T. Mathew and G. A.
Olah, J. Fluorine Chem., 2003, 123, 61.
environmentally benign alternative solvent for the nucleophilic
trifluoromethylation of aldehydes, ketones and oxazolidinone
in the presence of inorganic bases. Solvolysis of Me3SiCF3
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Hagiwara, H. Mochizuki and T. Fuchikami, Synlett, 1997, 587; (c) T.
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Kawano and H. Fujisawa, Chem. Lett., 2005, 34, 88; (f) Y. Kawano,
H. Fujisawa and T. Mukaiyama, Chem. Lett., 2005, 34, 422; (g) Y.
Kawano, N. Kaneko and T. Mukaiyama, Bull. Chem. Soc. Jpn., 2006,
79, 1133; (h) G. K. S. Prakash, C. Panja, H. Vaghoo, V. Surampudi,
R. Kultyshev, M. Mandal, G. Rasul, T. Mathew and G. A. Olah,
J. Org. Chem., 2006, 71, 6806; (i) S. Mizuta, N. Shibata, T. Sato,
H. Fujimoto, S. Nakamura and T. Toru, Synlett, 2006, 267; (j) S.
Mizuta, N. Shibata, S. Ogawa, H. Fujimoto, S. Nakamura and T.
Toru, Chem. Commun., 2006, 2575.
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Chem., 1992, 57, 1124; (b) J. D. O. Anderson, W. T. Pennington and
D. D. DesMarteau, Inorg. Chem., 1993, 32, 5079; (c) D. Borkin,
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(b) M. Doble, A. K. Kruthiventi, in Green Chemistry and Processes,
Academic Press, Burlington, MA, 2007; (c) V. K. Ahluwalia, in
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& Francis, Boca Raton, FL, 2008.
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by Solkaneꢀ 365mfc via fluorophilic attraction might be
responsible for this efficient transformation. It is highly ad-
vantageous that no environmentally harmful solvents, such
as chlorinated alkanes or DMF, are required in any of the
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processes and the products, catalysts and Solkaneꢀ 365mfc
are readily isolated, removed and recovered by simple filtration
and distillation, respectively. This is the first example of the
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use of Solkaneꢀ 365mfc as a medium in an organic reaction.
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We believe that Solkaneꢀ 365mfc will be a green halogenated
solvent for industrial use.16 Synthetic utility of this solvent will be
further demonstrated by organic reactions with non-fluorinated
reagents.
Acknowledgements
This study was financially supported in part by Grants-in-Aid
for Scientific Research (B) No. 21390030 (JSPS). We thank
TOSOH F-TECH INC. for the generous gift of Me3SiCF3, and
Dr Max Brawn and Mr Toyofuku, Yoshitaka, Solvay Fluor
10 F. M. Kerton, in Alternative Solvents for Green Chemistry, RSC
Publishing, Cambridge, UK, 2009.
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GmbH for the generous gift of Solkaneꢀ 365mfc.
11 (a) T. Welton, Chem. Rev., 1999, 99, 2071; (b) P. Wasserscheid and W.
Kein, Angew. Chem., Int. Ed., 2000, 39, 3772; (c) R. Sheldon, Chem.
Commun., 2001, 2399; (d) H. Zhao and S. V. Malhotra, Aldrichim.
Acta, 2002, 35, 75; (e) Ionic Liquid in Synthesis, ed, P. Wasserscheid,
T. Welton, 2nd edn, Wiley-VCH, Weinheim, 2008.
Notes and references
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15 See Solvey Solkaneꢀ 365 mfc brochure, http://www.
solvaychemicals.com/chemicals/.
16 While the Global Warming Potential (GWP) of DMF was calculated
to be quite small, the Photochemical Ozone Creation Potential
(POCP) can be calculated between 300 and 600 based on the hydroxyl
radical rate constant. This would suggest that DMF has a significant
potential to contribute to ground level ozone formation. On the other
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hand, the POCP coefficient of Solkaneꢀ365mfc is low, its impact
on smog creation is small, while its GWP is 890. See Canadian
Cataloguing in Publication Data, DMF, Canadian Environmental
Protection Act, 1999. Cat. no. En40-215/54E.
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