18-Fluorostearic acid

The infamous fluoroacetic acid and the equally toxic naturally occurring even-numbered co-fhiorinated fatty acids were discussed in detail earlier (7), and several reviews are available (34,44, 66). Although not counted as being natural in the earlier survey (7), 4-fluorothreonine (837) is now considered to be a bona fide natural metabolite of Streptomyces cattleya (893), the stereochemistry of which has been confirmed by synthesis (894). In addition to the five oo-fluorinated fatty acids presented earlier (7), new studies of the seed oil of Dichapetalum toxicarium have uncovered 16-fluoro-palmitoleic acid (838), 18-fluorostearic acid (839), 18-fluorolinoleic acid (840), 20-fluoroarachidic acid (841), 20-fluoroeicosenoic acid (842), 18-fluoro-9,10-epoxystearic acid (843) (895), (Z)-16-fluorohexadec-7-enoic acid (844), (Z)-18-fluoroocta-dec-9-enoic acid (845), and (Z)-20-fluoroicos-9-enoic acid (846) (896). 

Farnesol, F-00003 Farnesylic acid, see T-00205 Ferulic acid, see H-00304 Filfiline, in D-00199 Floionolic acid, in T-OOl96 16-Fluorohexadecanoic acid, F-00004 18-Fluorooctadecanoic acid, F-(KX)05 18-Fluoro-9-octadecenoic acid, F-00006 16-Fluoropalmitic acid, see F-00004 12-Fluoro-PGF2a, in F-00007 18-Fluorostearic acid, see F-00005 12-Fluoro-9,11,15-trihydroxy-5,13-prostadienoic acid, F-00007 )-cis-erythro (orm, in D-00145... 

Fluorinated acids and acid derivatives Fluorostearic acidic 9,10-Difluorostearic acid< Monofluoroundecanic acide Sodium monofluoroleate Methyl fluoroundecanate ... 

The g.l.c. separation of cis- and /m/w-epoxy-esters forms the basis of a new procedure for determining the proportion of cis- and tra/w-isomers in a mixture. The report that w-chloroperbenzoic acid can be used at 90 without decomposition in the presence of suitable radical inhibitors may be of value when epoxidizing alkenes of reduced reactivity. Several fluorostearic acids have been prepared by interaction of mesyloxy-acids with tetrabutyl-ammonium fluoride in acetonitrile. A procedure for methylation (by diazomethane in the presence of boron trifluoride) and demethylation (by reaction with sodium borohydride and iodine, followed by methanol), with retention of optical activity, could prove useful in the synthesis of compounds of known configuration. ... 

When 2-fluorostearic acid was used in the study in Question 4, none of the 9-hydroxy- or 10-hydroxy-decenoic acids was formed. Why was that ... 

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