Modern Methods to Prepare Monofluoroaliphatic Compounds
Published Online: 15 MAR 2011
Copyright © 2004 by Organic Reactions, Inc. Published by John Wiley & Sons, Inc.
How to Cite
Sharts, C. M. and Sheppard, W. A. 2011. Modern Methods to Prepare Monofluoroaliphatic Compounds. Organic Reactions. 21:2:125–406.
- Published Online: 15 MAR 2011
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.
- monofluoroaliphatic compounds;
- halogen fluoride additions;
- fluoroalkylamine reagent;
- organic halides;
- perchloryl fluoride;
- nitrosyl fluoride;
- electrophilic fluorination;
- hydrogen fluoride;