This paper is based on a book now in preparation, "Organic Fluorine Chemistry," W. A. Sheppard and C.M. Sharts. W. A. Benjamin, publisher, expected publication date 1968.2 Teflon® and Freon® are registered trademarks of the E. I. du " Vesprin®-foreign trademark. b Aristocort®-registered trademark of Lederle Laboratories.

Organic fluorine chemistry has been important since the 1930s. The development of fluorine chemistry during World War II is well documented. Fluorine chemistry emerged in the 1950s because of three events: Large‐scale research designed to synthesize fluorine‐containing rockets was initiated. A fluorine atom at a specific site in a steroid molecule was found to enhance beneficial pharmacological effects New analytical techniques evolved (e.g., GC and NMR). There are eight reactions important for preparation of monofluoroaliphatic compounds. Halogen addition to alkenes and alkynes Fluoroalkylamine reagent for replacement of a hydoxy group. Nitrosyl fluoride addition to an activated double bond Hypofluorites for electrophilic fluorination. Inorganic and heteroatom fluorides for replacement of halogen, hydroxyl, or ester groups Hydrogen fluoride for addition Perchloryl fluoride for hydrogen replacement Condensation of a monolfluorinated organic compound.

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The Raman spectra offluoroorganic compounds show specific emission bands for carbon-fluorine bonds in the range 500-800 wave numbers (car'). With very limited exceptions, biological materials do not contain carbon-fluorine bonds. Fluoroorganic compounds introduced into biological samples can be detected by a Raman emission signal.Normal mode C-F bond bands are observed: (1) at 710-785 cm for trifluoromethyl groups;(2) at 530-610 cm' fbr aromatic organofluorine bonds; (3) a range centered at 690 cm1 for difluoromethylene groups. Specific examples of normal mode C-F bond emissions for organofluorine compounds containing trifluoromethyl groups are: 1-bromopertluorooctane, 726 cm' ; perfiuorodecanoic acid, 730 cm' ; triperfiuoropropylamine, 750 cm' ; 1,3,5-ths-(trifiuoromethyl)-benzene, 730 cm; Fluoxetine (Prozac) commercial powdered pill at 782 cm1 . Compounds containing aromatic C-F bonds are: hexafiuorobenzene, 569 cm' ; pentafluoropyridine, 589 cm . Difluoromethylene groups: perfiuorodecalin, 692 car1; perfiuorocyclohexane, 691 car1Raman spectra were observed with a standard single monocbromator. The 510.8 nm light source was a copper-vapor laser operated at 3-10 watts with 10-12 nanosecond pulses at 10 kHz repetition rate. Detection was made with a time-gated photomultiplier tube. Resonance Raman spectra were also observed at 255.4 nm using a frequency doubling crystal. Observed spectra were free offluorescence with very sharp strong C-F lines.

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