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Syntheses of Diphenic Anhydride-Mercury Compounds and Their Reaction with Nucleophilic Reagents
Takahashi, Teruo,Togashi, Shigeo,Morishita, Muneo,Takeda, Shiro
, p. 3020 - 3023 (2007/10/02)
Diphenic acid anhydride (1) is decarbonylated by prolonged heating with mercuric oxide (HgO) in acetic acid to give a diphenic anhydride-mercury compound (3).Since its infrared spectrum showed a shift of carbonyl adsorption to a very low wave number, the O-Hg linkage was considered to be in an ionic form (3'), with the carbon bonded to mercury becoming a carbonium ion.If this is the case, the compound would be expected to react with nucleophilic reagents and indeed 3 is reactive to KI, H2S and KCN.Keywords-diphenic anhydride-mercury compound; mercuration; carbon-mercury bond; carbonyl adsorptions; nucleophilic; the reaction mechanism; protonation
