Mercuric acetate, reaction with

The cyclized analog of meralluride is prepared by a similar synthesis. Thus, condensation of camphoric acid (42) (obtained by oxidation of camphor) with ammonia gives the bicyclic succinimide (44). Reaction with allyl isocyanate followed by ring opening and then reaction with mercuric acetate affords the mercury derivative (45) as the acetate rather than the hydroxide as above. Reaction with sodium chloride converts that acetate to the halide (46). Displacement on mercury with the disodium salt of thioglycollic acid affords the diuretic mercaptomerine (47). ... 

Acetamido-4-inethylselenazole. reaction with formaldehyde, 231 reaction with mercuric acetate. 231 Acetanilidovinyl derivatives, of thia-... 

Alkenylmercury compounds can be prepared by hydroboration of an alkyne with catecholborane, followed by reaction with mercuric acetate.185... 

The hemidecarboxylation of sodium phthaiate on reaction with mercuric acetate in boiling water [Eq. (82), X = H] (90) was the first reported thermal decarboxylation. The reaction has been observed for a number of arenes with two adjacent carboxylate groups (1-4,91) and has been named the Pesci reaction (91). Studies of 3-substituted sodium phthalates or of preformed mercuric 3-substituted phthalates have shown that the sterically hindered carboxyl group (the 2-carboxyl) is preferentially eliminated whether X is electron-donating or electron-withdrawing [Eq. (82), X = Me (91), Cl, N02 (91,93), Br (93), or C02H (94)]. A similar conclusion was drawn from the decomposition of mercuric 1,2-naph-thalenedicarboxylate and 3,4-phenanthrenedicarboxylate (91). 

Cyclohexyl ine, 52, 727 reaction with acetaldehyde, 50,67 Cyclooctatretraene, chlorination, 50, 36 reaction with mercuric acetate, 50, 24 CYCLOOCTENE, 1-NITRO, 50,54 CYCLOPENTANECARBOXALDE-HYDE, l-PHENYL-,51,24 Cyclopentane-1,3-dione, 52,4 CYCLOPENTYLAMINE, 1-PHENYL-, 51,45... 

The dithiolothiadiazolothione 41 was oxidized to the ketone 40 following reaction with mercuric acetate (Scheme 7) <1993SM(68)1914>. 

Acyl-2-methylthio-l,6,6a lv-trithiapentalenes, on reaction with mercuric acetate, undergo a degradation leading to a dithiolylidene ketone (Eq. 16).46... 

Siloxycyclopropanes are quantitatively converted into )5-acetoxymercuriketones by reaction with mercuric acetate. Successive treatment with PdCl2 or PdCl2 + CO gives a-methyleneketones or y-ketoesters, respectively. The ring cleavage takes place highly selectively at the least substituted cyclopropane carbon atom (equation 60) . 

Monomethylaminonaphthalene-6-sulphonio acid, reaction with mercuric acetate, 134. 

Acetoxylation. Treibs found that olefins and ketones can be acetoxylated by reaction with mercuric acetate. Initially the reaction was conducted without solvent... 

Oxazolidines are obtained in good to excellent yields by the palladium(II)-catalyzed cyclization of A-Boc protected iV-allyl-A -hydroxymethylamines (191) <94CC357>. The palladium species is regenerated by molecular oxygen in DMSO (Scheme 94). Allyl carbamoylmethyl ethers cyclize to oxazolidines by reaction with mercuric acetate <89H(28)663>. Silver triflate catalyzes the cyclization of (9-propargyl isoureas to 4-alkylidene-oxazolidines with high diastereoselectivity <88CC1175>. 

Transannular cyclization. In a recent total synthesis of indole and dihydroindole alkaloids,3 a key step is a transannular cyclization reaction with mercuric acetate. For example, the reaction of 4/3-dihydrocleavamine (1) with mercuric acetate yields the indolenine (2), which was isolated as the more stable reduction product (3). 

Aromatic hydrocarbons can be brought into reaction with mercuric acetate by boiling the mixture for several hours under reflux, which gives, for instance, an 80% yield of phenylmercuric acetate and the yield is increased to 92% if these components are heated in glacial acetic acid under pressure at 110°189... 

Cyclization to the pentacyclic Aspidosperma series could be accomplished by two alternative routes reaction with mercuric acetate or oxygen in the presence of a platinum catalyst in this way, vincadifformine (2) and minovine (506) were produced (Scheme 30). 

Camphoric acid on condensation with ammonia and subsequent treatment with allyl isocyanate aflfords an intermediate which on reaction with mercuric acetate in methanol gives rise to the corresponding mercury derivative as acetate. This on treatment with sodium chloride followed by sodium thioglycollate in aqueous NaOH solution yields the offieial eompound which may be obtained either by evaporation or by preeipitation with an appropriate solvent. 

Not surprisingly diazocyclopentadiene readily undergoes electrophilic substitution reactions. Attack takes place preferentially at the 2- and 5-positions, presumably because this involves a more stable transition state than does attack at the 3,4-positions [68]. Thus nitration by means of benzoyl nitrate in acetonitrile produces both 2- and 3-nitrodiazocyclopentadienes, but the two products are formed in the ratio of 2 1 [68]. Reaction with mercuric acetate... 

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