Organomercury compounds. XXVIII the synthesis and 199Hg N.M.R. spectra of some unsymmetrically dimercurated arenes

Glen B. Deacon, J. Maxwell O’Connor, Geoffrey N. Stretton

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Abstract

Mercuration of 1-methoxy-2-nitrobenzene (1) with mercuric trifluoroacetate (mole ratio 1:1) in trifluoroacetic acid yields 1-methoxy-2-nitro-4-(trifluoroacetatomercurio)benzene (2). With a 1:2 mole ratio, (2) and 1-methoxy-2-nitro-4, 6-bis(trifluoroacetatomercurio)benzene (3) are obtained, and, with a 1:4 ratio, (3) and a little 1-methoxy-2-nitro-3, 4-bis(trifluoroacetatomercurio)benzene (4). are obtained. 2-Nitrophenol (5) with mercuric trifluoroacetate (mole ratio 1:2) gives 2-nitro-4, 6-bis(trifluoroacetatomercurio)phenol (6), and vanillin (7) yields 5, 6-bis(trifluoroacetatomercurio)vanillin (8). Compound (8) has been converted into 5, 6-di(chloromercurio)- and 5, 6-di(bromomercurio)vanillin [(9) and (10)]. 199Hg, 199Hg spin-spin coupling constants have been determined as 6500-8200 Hz for 3 JHg, Hg of (8)-(10), 2100-2200 Hz for 4 JHg, Hg of (3) and (6), and 858 Hz for 5 JHg, Hg of 4-methoxy-2, 5-bis(trifluoroacetatomercurio)benzoic acid (11). 

Original languageEnglish
Pages (from-to)953-961
Number of pages9
JournalAustralian Journal of Chemistry
Volume39
Issue number7
DOIs
Publication statusPublished - 1986

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