4070
J. Legros et al. / Tetrahedron 58 42002) ꢀ067±ꢀ070
chromatography .pentane/Et O, 90:10 then 70:30) allowed
2
the isolation of a sample of each pure ketoneꢀ
Hꢀ; Nakano, Tꢀ; Ishii, Fꢀ; Sato, Sꢀ .Kanto Denka Kogyo Coꢀ,
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8
2
0
.2.1. 3-Tri¯uoromethylcyclohexan-1-one ꢀ2). Colorless
4
liquid: IR n .cm ) 1717; F NMR d 274ꢀ1 .d,
2
1
19
1
13
JH±F8ꢀ0 Hz), HNMR d 1ꢀ6±2ꢀ7 .m); C NMR d 207ꢀ2,
9ꢀ .a) Sheppard, Wꢀ Aꢀ J. Am. Chem. Soc. 1965, 87, 2410±2420ꢀ
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1
2
1
CF CH), 40ꢀ5, 39ꢀ7 .q,
2
26ꢀ5 .q,
J
278 Hz, CF ), 42ꢀ1 .q, JC±F28 Hz,
C±F
3
3
J
2ꢀ0 Hz, CF CHCH CO),
3
C±F
3
2
3
3ꢀ5 .q, J 2ꢀ5 Hz, CF CHCH ), 23ꢀ4ꢀ
C±F
3
2
2
.2.2. 4-Tri¯uoromethylcyclohexan-1-one ꢀ3). Colorless
0
4
liquid: IR n .cm ) 1719; F NMR d 273ꢀ2 .d,
10ꢀ .a) Sheldon, Rꢀ Aꢀ; Dakka, Jꢀ Catal. Today 1994, 19, 215±245ꢀ
.b) Sheldon, Rꢀ Aꢀ; Kochi, Jꢀ Kꢀ Metal-Catalyzed Oxidations of
Organic Compounds; Academic: New York, 1981ꢀ .c) Shilov,
Aꢀ Eꢀ Activation of Saturated Hydrocarbons by Transition
Metal Complexes; Dꢀ Reidel Publishing Co: Dordrecht,
2
1
19
1
13
JH±F8ꢀ0 Hz), HNMR d 1ꢀ6±2ꢀ7 .m); C NMR d 208ꢀ9,
1
2
1
27ꢀ2 .q,
J
278 Hz, CF ), 40ꢀ1 .q, JC±F28 Hz,
C±F
3
3
CF CH), 40ꢀ0, 24ꢀ7 .q, J 2ꢀ5 Hz, CF CHCH )ꢀ
3
C±F
3
2
1
984ꢀ .d) Hill, Cꢀ Lꢀ Activation and Functionalization of
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Raja, Rꢀ; Thomas, Jꢀ Mꢀ Angew. Chem. Int. Ed. 2000, 39,
2310±2313ꢀ
Acknowledgements
We thank Drs Negishi and Katsuhara .Central Glass Coꢀ,
Ltd) for their interest in this workꢀ We also thank the
European Contract of Research Training Network
.`Fluorous Phase' HPRN CT 2000-00002) and the European
Union .COST-Action `Fluorous Medium' D12/98/0012)ꢀ
11ꢀ Naota, Tꢀ; Takaya, Hꢀ; Murahashi, Sꢀ Iꢀ Chem. Rev. 1998, 98,
2599±2660ꢀ
1
2ꢀ Nomura, Kꢀ; Uemara, Sꢀ J. Chem. Soc., Chem. Commun. 1994,
29±130ꢀ
1
3ꢀ Carlsen, Hꢀ J. Synth. Commun. 1987, 17, 19±23ꢀ
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