Aromaticity hetarynes

During this period of time we, and a number of other research groups, have been investigating the reactions of highly halogenated aiynes and hetarynes with aromatic hydrocarbons, for the reasons outlined in the introduction. In a reaction of pentafluorophenylmagnesium chloride with ethylene oxide in the presence of benzene, it was shown that, as well as 3-pentafluorophenylethanol (23) a by-product of molecular formula C12H6F4 was produced 43>. 

Other species which will be considered within the scope of this chapter (Sections III.l.C and III.2.D) include 16 and 17, formally derived (Section I.2.A) from the maleic acid derivatives 18 and the quinoidal compounds 19. Since these precursors are not actually aromatic, 16 and 17 cannot be considered true hetarynes. Nevertheless, the similarity of the orbital representations... 

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