Mercury nitrate reaction with alkenes

Vicinal hydroxy carbamates are prepared by the osmium-catalyzed reaction of alkenes with A-chloro-A-metallocarbamates generated in situ from A-chloro-A-sodiocarbamates (easily prepared from the carbamate, tert-butyl hypochlorite, and sodium hydroxide in methanol) by reaction with silver nitrate77 or mercury(II) salts78 in acetonitrile, The greatest reactivity was, however, displayed by the A-chloro-A-sodiocarbamate/mercuryUI) nitrate/tetraethylam-monium acetate (relative ratio 1.5 0.75 1) system, unfortunately low yields of hydroxycarba-mates from trisubstituted alkenes were obtained, due to competitive formation of organomer-... 

Acetamido-3,4-di-61-acetyl-6-deoxy-D-glucal on reaction with ammonium nitrate-trifluoroacetic anhydride in aqueous sodium bicarbonate affords the unsaturated pentose compound 31 whereas reaction with mercury(II) sulfate and sulfuric acid gave the expected -alkene 32. ... 

Reaction of an alkene with mercury(II) nitrate and nitriles, usually acetonitrile, followed by hydrolysis, gave /J-acylamino mercury(II) salts, which were isolated in good yield as the corresponding chlorides after treatment with sodium chloride (Table 2)29 32. 

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