Standard Article

Modern Methods to Prepare Monofluoroaliphatic Compounds

  1. Clay M. Sharts1,
  2. William A. Sheppard2

Published Online: 15 MAR 2011

DOI: 10.1002/0471264180.or021.02

Organic Reactions

Organic Reactions

How to Cite

Sharts, C. M. and Sheppard, W. A. 2011. Modern Methods to Prepare Monofluoroaliphatic Compounds. Organic Reactions. 21:2:125–406.

Author Information

  1. 1

    San Diego State University, San Diego, California

  2. 2

    E. I. du Pont de Nemours and Co., Inc., Central Research Department, Wilmington, Delaware

Publication History

  1. Published Online: 15 MAR 2011

Abstract

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:

  1. Large-scale research designed to synthesize fluorine-containing rockets was initiated.

  2. A fluorine atom at a specific site in a steroid molecule was found to enhance beneficial pharmacological effects

  3. New analytical techniques evolved (e.g., GC and NMR).

There are eight reactions important for preparation of monofluoroaliphatic compounds.

  1. Halogen addition to alkenes and alkynes

  2. Fluoroalkylamine reagent for replacement of a hydoxy group.

  3. Nitrosyl fluoride addition to an activated double bond

  4. Hypofluorites for electrophilic fluorination.

  5. Inorganic and heteroatom fluorides for replacement of halogen, hydroxyl, or ester groups

  6. Hydrogen fluoride for addition

  7. Perchloryl fluoride for hydrogen replacement

  8. Condensation of a monolfluorinated organic compound.

Keywords:

  • preparation;
  • monofluoroaliphatic compounds;
  • halogen fluoride additions;
  • fluoroalkylamine reagent;
  • monofluorosubstitution;
  • organic halides;
  • esters;
  • alcohols;
  • perchloryl fluoride;
  • nitrosyl fluoride;
  • electrophilic fluorination;
  • hypofluorites;
  • hydrogen fluoride;
  • condensation;
  • monofluorination