Fluorine Chemistry. Biological Effects of Organic Fluorides by J. H. Simons

By J. H. Simons

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1956), Wakai and Prickman (1954), W a r d and H e n c h (1955), West (1958), and W e s t and Cervoni (1955).

T h e toxicities of ω-carboxylic esters of the general formula F(CH2)^C02R fluctuated with increasing values of n; where η is odd the c o m p o u n d is highly toxic, whereas w h e n η is even the toxicity is considerably less. -fluoropropionic acid ; at least F A c could not be the end product of β-oxidation. Other ω-fluoro c o m p o u n d s containing the fundamental carbon chain of toxic m e m b e r s b u t which could not undergo β-oxidation proved to be relatively n o n ­ toxic. For example, ethyl y-fluorobutyrate is highly toxic b u t ethyl yfluoro-j8j8-dimethylbutyrate was found to be nontoxic.

T h e 2-fluoroethyl c o m p o u n d in any series has proven to b e consider­ ably less toxic t h a n t h e higher even m e m b e r s in t h e same series. Possibly the influence of t h e 2-fluorine atom o n other functional groups a n d their metabolic behavior outweighs solubility a n d steric effects. Additional references are as follows: Pattison (1957) a n d Walker a n d Parker (1958). 1 Phosphofluoridates T h e biological effects of certain fluorophosphates recorded by L a n g e and Kreuger in 1932 were exploited in t h e search for new chemical war­ fare agents during W o r l d W a r I I ( M c C o m b i e a n d Saunders, 1946 b ; 1 W e a r e grateful t o D r s .

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