Main Group-conjugated Organic Anion Chemistry. 1. Synthesis of Magnesium Anthracene, Silylated Anthracenes, or Fluoranthene Tetrahydrofuran and Tertiary Amine Complexes and of Magnesium Cyclooctatetraene: X-ray Structure of [mgl(TMEDA)]*[mgL(THF)2] (L = 9,10-Bis(trimethylsilyl) Anthracene)

Teresa Alonso, Stephen Harvey, Peter C. Junk, Colin L. Raston, Brian W. Skelton, Allan H. White

Research output: Contribution to journalArticle

36 Citations (Scopus)

Abstract


Mg(An)(THF)3(1, THF = tetrahydrofuran) decomposes in toluene or benzene to Mg(An)(THF)2(5) and then to elemental magnesium. Mg(An)(THF)(TMEDA) (6), prepared from its constituents or by treating 1 with TMEDA, and Mg(An)(PMDETA) (7) and Mg(An){(-)-sparteine) (8), prepared by treating 1 with the appropriate amine, are stable in these solvents (An = anthracene, TMEDA = N,N,N ‘,N’-tetra-methylethylenediamine, PMDETA = N,N,N',N'',N''-pentamethyldiethylenetriamine). Mg(AnSiMe3)-(TMEDA) ((9, AnSiMe3= 9-(trimethylsilyl)anthracene) and Mg{An(SiMe3)2) (TMEDA) (10, An(SiMe3)2= 9,10-bis(trimethylsilyl)anthracene) form on adding excess TMEDA to Mg(AnSiMe3)(THF)2(3) and Mg{An(SiMe3)2)(THF)2(4), either prepared by treating the substituted anthracenes with magnesium or 1 in THF; 9 and 10 react with THF yielding Mg(AnSiMe3)(THF)(TMEDA) (11) and 4 in equilibrium with 10. Mg(Fl)2(THF)6(12), prepared from magnesium and FI (= fluoranthene) or FI and 1 in THF, slowly decomposes in TMEDA to magnesium metal and fluoranthene. Mg(COT)(THF)2.5 (13) has also been prepared from 1 and COT and via an anthracene-catalyzed reaction of magnesium and COT (= cyclooctatetraene). Recrystallization of 4 from a mixture of THF and TMEDA gave the 1:1 crystalline complex 4:10, as shown by an X-ray structure determination; the discrete molecules of 4 and 10 have each magnesium attached to the C-9 and C-10 anthracene carbon centers, Mg-C = 2.218and 2.223A, respectively.

Original languageEnglish
Pages (from-to)2110-2116
Number of pages7
JournalOrganometallics
Volume6
Issue number10
DOIs
Publication statusPublished - 1 Oct 1987
Externally publishedYes

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