2,2-diphenyl-2λ5-phospha-phenalenyl-und 2,2-dimethyl-2λ5-phospha-indenyl-lithium

Hubert Schmidbaur, Albert Mörtl

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Abstract

From the reaction of 1,8-bis(bromomethyl)naphthalene with diphenyl(trimethylsilyl)phosphine a cyclic phosphonium salt IX is formed which can be rearranged with (CH3)3PCH2 to yield the cyclic ylide X. Its metallation with t-butyllithium gives 2,2-diphenyl-2λ5-phospha-phenalenyl-lithium XI. The anion of XI cannot be seen as a delocalized phospha-phenalenyl π-system but rather as a phosphonium-bis-ylide similar to the diphenylphosphonium-bis-benzylide. From 1,2-bis(chloromethyl)benzene and (C6H5)2PSi(CH3)3 or from 1,2-bis(chloromagnesiummethyl)benzene and CH3PCl2, followed by quaternization using CH3Br, cyclic phosphonium salts (XII and XV, respectively) can also be obtained, which may again be rearranged to form the ylides XIII or XVI. XVI gives with (CH3)3CLi 2,2-dimethyl-2λ5-phospha-indenyl-lithium XVII, containing a dimethyl-phosphonium-bis-ylide anion ("isophosphindolyl-lithium").

Original languageGerman
Pages (from-to)171-182
Number of pages12
JournalJournal of Organometallic Chemistry
Volume250
Issue number1
DOIs
StatePublished - 5 Jul 1983
Externally publishedYes

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