Difunctionalization of primary aromatic amines with ethylene; synthesis of μ-arylnitrilobis(ethane-2,1-diyl)dimercury(II) complexes. Crystal structure of 2,4,6-Me3C6H2N-(CH2CH2HgCl)2

G. B. Deacon, B. M. Gatehouse, L. W. Guddat, S. C. Ney

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Abstract

Reaction of primary aromatic amines, mercuric acetate, and ethylene in tetrahydrofuran under pressure (ca. 40 atm) yields the organomercurials ArN(CH2CH2-HgOAc)2 (Ar = Ph, 2-ClC6H4, 3-ClC6H4, or 4-ClC6H4) or, after treatment of the crude products with sodium halide, ArN(CH2CH2HgX)2 (Ar = 4-MeC6H4, 4-MeOC6H4, or 2,4,6-Me3C6H2, X = Cl; Ar = 2,4-Cl2C6H3, 2,6-Cl2C6H3, or 2,4,6-Br3C6H2, X = Br). The X-ray diffraction study of 2,4,6-Me3C6H2N(CH2CH2HgCl)2 shows the molecules to have near linear C-Hg-Cl stereochemistry, and to be arranged in centrosymmetric dimers with weak Hg ··· Cl intermolecular bonding.

Original languageEnglish
Pages (from-to)1-4
Number of pages1
JournalJournal of Organometallic Chemistry
Volume375
Issue number1
DOIs
Publication statusPublished - 3 Oct 1989

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