Acetylides mercury acetylide

Alkynyl anions are more stable = 22) than the more saturated alkyl or alkenyl anions (p/Tj = 40-45). They may be obtained directly from terminal acetylenes by treatment with strong base, e.g. sodium amide (pA, of NH 35). Frequently magnesium acetylides are made in proton-metal exchange reactions with more reactive Grignard reagents. Copper and mercury acetylides are formed directly from the corresponding metal acetates and acetylenes under neutral conditions (G.E. Coates, 1977 R.P. Houghton, 1979). 

Propargyl bromide forms explosive metal acetylides when copper or its alloys, silver or mercury are present. 

For equipment handling acetylene the pure metals, or alloys containing copper, silver, mercury, gold, must be avoided to prevent the formation of explosive acetylides. 

Silver nitrate (or other soluble salt) reacts with acetylene in presence of ammonia to form silver acetylide, a sensitive and powerful detonator when dry. In the absence of ammonia, or when calcium acetylide is added to silver nitrate solution, explosive double salts of silver acetylide and silver nitrate are produced. Mercury(I) acetylide precipitates silver acetylide from the aqueous nitrate. 

There is a danger of explosion in contact with copper, high-copper alloys, mercury or silver (arising from metal acetylide formation). 

Contact of acetylene with the nitrate solution gives mercury acetylide, an explosive sensitive to heat, friction or contact with sulfuric acid. 

Acetylenic compounds with replaceable acetylenically bound hydrogen atoms must be kept out of contact with copper, silver, magnesium, mercury or alloys containing them, to avoid formation of explosive metal acetylides. 

Catalytic forms of copper, mercury and silver acetylides, supported on alumina, carbon or silica and used for polymerisation of alkanes, are relatively stable [3], In contact with acetylene, silver and mercury salts will also give explosive acetylides, the mercury derivatives being complex [4], Many of the metal acetylides react violently with oxidants. Impact sensitivities of the dry copper derivatives of acetylene, buten-3-yne and l,3-hexadien-5-yne were determined as 2.4, 2.4 and 4.0 kg m, respectively. The copper derivative of a polyacetylene mixture generated by low-temperature polymerisation of acetylene detonated under 1.2 kg m impact. Sensitivities were much lower for the moist compounds [5], Explosive copper and silver derivatives give non-explosive complexes with trimethyl-, tributyl- or triphenyl-phosphine [6], Formation of silver acetylide on silver-containing solders needs higher acetylene and ammonia concentrations than for formation of copper acetylide. Acetylides are always formed on brass and copper or on silver-containing solders in an atmosphere of acetylene derived from calcium carbide (and which contains traces of phosphine). Silver acetylide is a more efficient explosion initiator than copper acetylide [7],... 

Mercury(II) acetylide, 0975 Mercury bis(chloroacetylide), 1356 3-Methyl-3-buten-1 -ynyltriethyHead, 3413 Monocaesium acetylide, 0661 Monolithium acetylide, 0673... 

Several explosive salts including the acetylide, azide, borate, bromate, chlorate, chromate, iodate (and ammonium iodate double salt), nitrite, perchlorate (and ammonium perchlorate double salt), periodate, permanganate, picrate and trinitrobenzoate were prepared. The 3 latter salts and the acetylide, azide and bromate are impact-sensitive detonators [1], It appears probable that many of the explosively unstable compounds [2], formed in various ways from interaction of mercury or its compounds with ammonia or its salts, may have the common polymeric structure now recognised for Millon s base [3], This is a silica-like network of N+ and Hg in 4- and 2-coordination, respectively, with OH and water in the interstitial spaces. Individually indexed compounds are Poly(dimercuryimmonium acetylide)... 

This class of compounds showing explosive instability deals with heavy metals bonded to elements other than nitrogen and contains the separately treated groups GOLD COMPOUNDS LEAD SALTS OF NITRO COMPOUNDS LITHIUM PERALKYLURANATES MERCURY COMPOUNDS METAL ACETYLIDES METAL FULMINATES METAL OXALATES PLATINUM COMPOUNDS PRECIOUS METAL DERIVATIVES SILVER COMPOUNDS... 

Dbnerciuy dicyanide oxide, 0983 Dimetbybnercuiy, 0907 Dipbenybnerciuy, 3480 Dipropybnerciuy, 2537 2-Hydroxyetbybnercuiy(ll) nitrate, 0857 Mercury(ll) acetylide, 0975 Mercuiy(II) amide chloride, 3999 Mercury(l) azide, 4612... 

Lithium 3-(l,l,2,2-tetrafluoroethoxy)propynide, Lithium trifluoropropynide, 1046 Manganese(II) bis(acetylide), 1396 Mercury(ll) acetylide, 0975... 

Several preparative methods exist for the synthesis of 3(2//)-dihydrofuranones. 2,5-Disubstituted or 2,2,5,5-tetrasubstituted 3(2i/)-dihydrofuranones are usually prepared by reaction of sodium or lithium acetylide with a ketone to yield an alkynic alcohol which is then treated with a carbonyl compound in the presence of base to afford alkynic diols. Mercury catalyzed hydration of the resultant diols in the presence of acid affords the furanones in good yields (76JMC709). 

The initiations achieved in the early work of Henderson (Ref 1) and Poole (Refs 2 3) with nitrogen iodide by a - particles, Kallmann and Schankler (Ref 9) with TNT, MF, NC, picrates and azides by intense beams of hydrogen, argon and mercury ions and also by electrons, and Muraour (Ref 10) with Ag acetylide by high speed electrons, brought forth the possible solution that the expins were caused by activation of a few neighboring molecules... 

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