Difluoroalkylation of carbonyl compounds with (1,1-Difluoroalkyl)silane derivatives

Synlett

Volumn 1995, Issue 7, 1995, Pages 717-718

  Hagiwara, Toshiki ^a   Fuchikami, Takamasa ^a  

^a SAGAMI CHEMICAL RESEARCH CENTER   (Japan)

Author keywords

(1,1 Diflluoroalkyl)silanes; (Difluoromethyl)silanes; Carbonyl Compounds; Difluoroalkylation; Difluoromethylation

Indexed keywords

EID: 85064695108     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-1995-5070     Document Type: Article

References (9)

1. Prakash, G. K. S.; Krishnamurti, R.; Olah, G. A. J. Am. Chem. Soc, 1989, 111, 393.
2. Krishnamurti, R.; Bellew, D. R.; Prakash, G. K. S. J. Org. Chem., 1991, 56, 984.
3. Stahly, G. P.; Bell, D. R. J. Org. Chem., 1989, 54, 2873.
4. Urata, H.; Fuchikami, T. Tetrahedron Lett., 1991, 32, 91.
5. Fuchikami, T.; Ojima, I. J. Organomet. Chem., 1981, 2i2, 145.
6. MOPAC Ver.6, Stewart, J. J. P. QCPEBulL, 1989, 9, 10
7. 2, 2-diiluoro-l-phenylethanol (6): 1H-NMR (CDCI3, TMS) 5= 2.1-2.6 (b, 1H), 4.83 (td, J=10 Hz, 5 Hz, 1H), 5.77 (td, J=56 Hz, 5 Hz, 1H), 7.3-7.5 (m, 5H); l9F-NMR (CDCI3, CFCI3) 6=-128.6 (ddd, J=280 Hz, 56 Hz, 11 Hz, IF),-126.3 (ddd, J=280 Hz, 56 Hz, 11 Hz, IF); MS m/e (relative int.) 158(8), 107(100), 79(86), 77(56), 51(28), 18(20)
8. Broicher, V.; Geffken, D. J. Organomet. Chem., 1990, 381, 315.
9. 2, 2-difiuoro-l-phenylbutanol(7): IH-NMR (CDCI3, TMS) 6= 1.00 (t, J=7.5 Hz, 3H), 1.5-2.1 (m, 2H), 2.47 (d, J=3.8 Hz, 1H), 4.86 (td, J=10 Hz, 3.8 Hz, 1H), 7.3-7.5 (m, 5H); 19F-NMR (CDCI3, CFCI3) 6=-112.9 (dddd, J=246Hz, 22 Hz, 14 Hz, 10 Hz, IF),-112.2 (dddd, J=246 Hz, 22 Hz, 13 Hz, 10 Hz, IF) 2, 2-difluoro-3-methyl-l-phenylbutanol (8): 19F-NMR (CDCI3, CFC13) 6=-120.3 (ddd, J=249 Hz, 20 Hz, 7.7 Hz, IF),-118.0 (ddd, J=249 Hz, 18 Hz, 10 Hz, IF)