Sechoing. Lin, Jack M. Miller
Feb 1, 1977
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0
Influential Citations
13
Citations
Journal
Journal of Fluorine Chemistry
Abstract
Abstract Decomposition and side reactions of pentafluorophenylmagnesium bromide and pentafluorophenyllithium, when used in syntheses, have been investigated using GC/MS techniques. Reactions with reagents such as C 6 F 5 X (X = H, F, Cl, Br, I), C 6 F 4 X 2 (X = H, Cl), C 6 F 3 Cl 3 , C 6 H 6 , (C 6 X 5 ) 3 P (X = H, F), (C 6 X 5 ) 3 P=O (X = H, F), (C 6 X 5 )Si(CH 3 ) 3 (X = H, F) and (CH 3 ) 4-n SiCl n , n = 1, 2, in ether or ether/n-hexane were studied. In addition to the principal reaction of synthetic use, namely the replacement of a halogen by a pentafluorophenyl group, two types of side reactions were observed. These were (i) intermolecular loss of LiF via a nucleophilic substitution, and (ii) intramolecular loss of LiF, followed by the addition of either, inorganic salts such as lithium or magnesium halides, or organometal compounds such as organolithium or Grignard reagent present in the system. GC/MS proved to be an ideal method of monitoring such organometallic reaction systems, although it was sometimes not possible to identify byproducts as a particular isomer.