By Jean-Pierre Bégué
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However, it is rather difficult to determine if these hydrogen bonds really exist: other factors may stabilize the conformation corresponding to the short HÁ Á ÁF interatomic distance observed. 20 13 14 GENERAL REMARKS ON STRUCTURAL, PHYSICAL, AND CHEMICAL PROPERTIES role of an HÁ Á ÁF bond in the interactions between fluorinated substrates and biological macromolecules still remain an open question (cf. Chapter 3). 5). If the fluorine atom itself is only slightly involved in hydrogen bonds, its inductive effect plays a very important role in the ability of neighboring functional groups to give or to accept hydrogen bonds.
F. L. Hermann, and G. Boche, Angew. Chem. Int. Ed. 2006, 45, 823. 40. B. Farnham, Chem. Rev. 1996, 96, 1633. 41. J. Y. Yang, Tetrahedron 1992, 48, 189. 42. J. A. D. G. , Wiley, Hoboken, NJ, 1992, p. 205. S. K. Yudin, Chem. Rev. 1997, 97, 757. P. M. Shreeve, Tetrahedron 2000, 56, 7613. 43. J. Burton and L. Liu, Fluorinated organometallic compounds in organic chemistry, in Current Topics in Chemistry No. D. , Springer, Berlins, 1997, p. 45. G. J. OReilly, J. Org. Chem. 1987, 52, 2481. 44. G. J. Stewart, and P.
28 Preparation and reaction of trimethylsilyldiﬂuoroacetate. Remarks: Preparation of difluorophosphonates. The preparation of difluorophosphonates is detailed in Chapter 7 (enzyme inhibitors). 124 Preparation of gem-difluoroallenes. 127 However, they are not valuable at the laboratory level: SF4 is toxic and hazardous, and special apparatus is required to utilize HF. On a bench scale, oxidative desulfurization-fluorination allows the transformation of dithiocarbonates and xanthates into —CF3 or –OCF3 groups.