Add time:07/31/2019         Source:sciencedirect.com

m- and p-Chlorinated ω-phenoxyalcohols 1, were transformed into the corresponding lithium ω-(m- and p-lithiophenoxy)alkoxides 4, respectively, by successive deprotonation with n-butyllithium and subsequent chlorine–lithium exchange by lithium naphthalene radical anion in THF–methylcyclohexane. Lithium 2-(4-lithiophenoxy)ethoxide (4a′) was also prepared by bromine–lithium exchange of 2-(4-bromophenoxy)ethanol (2a′) with two equivalents of n-butyllithium. The organolithiums were modified with magnesium 2-ethoxyethoxide in order to avoid ortho-metallation of the above-mentioned substituted arenes. Subsequent reaction of these intermediates with the electrophiles carbon dioxide, benzophenone, benzonitrile and 0.5 equivalents of mercuric chloride yielded the expected m- and p-substituted (ω-hydroxyalkoxy)benzenes in yields ranging from 50 to 75%. The crystal structures of the organomercurials 8a′ and 8b′ have been determined and revealed the Hg atom to occupy a crystallographic center of symmetry in a linear CHgC arrangement.

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