Carbon oxysulphide, reaction

The reaction of carbon oxysulphide with a-aminonitriles results in 5-amino-2-hydroxy thiazoles these are structurally similar to the 2-mercaptothiazoles but are found to be less stable, readily undergoing cleavage or rearrangement to give 4-thiohydantoins. Thus the reaction between ethyl aminocyanoacetate and carbon oxysulphide 31 in ether afforded 5-amino-2-hydroxy-4-carbethoxythiazole 32, which in the presence of aqueous ammonia was converted into 5-carbethoxy-4-thiohydantoin 33. When using sodium... 

The nitrones (119) are readily converted into thiolactams (120) by heating under reflux in carbon disulpWde. The reaction presumably involves an initial cycloaddition and subsequent cycloreversion with the loss of carbon oxysulphide. 

A general approach to both saturated and unsaturated thioesters consists of reaction between phosphorus ylides and carbon oxysulphide (Scheme 46). °... 

Further investigations into the reactisulphur atoms with olefins to yield thiirans have established absolute rate constants and a n ative temperature dependence on the rate constants for the reaction of sulphur in its state, obtained by flash i otolysis of carbon oxysulphide, with... 

Hydroxycoumarin condenses with 3-methylthio-5-phenyl-l,2-dithiO lium salts to give the complex dithiolylidene ketone (36 R = Ph), required for comparison with the product (36 R = Me) obtained by treatment of the pyranocoumarin (37) with boron sulphide." The base-catalysed reaction of 5-methylene-l,2-dithiole-3-thiones with carbon oxysulphide leads, after methylation of the intermediates, to mixtures of two types of product, (38) and (39)." ... 

About 1865, E. Kopp, and P. W. Hofmann tried to revive the oxysulphide theory, but J. Pelouze refuted their arguments and after a long study of the reactions, J. Kolb confirmed A. Scheurer-Kestner s work, but concluded that in the main reaction the calcium carbonate loses its carbon dioxide by the action of the carbon dioxide in the fire gases. A. Scheurer-Kestner then showed that in this last conclusion J. Kolb is in error, because black ash can be made in crucibles without any assistance from the fire gases that the decomposition of the calcium carbonate, even in the presence of coal, requires a higher temp, than the reduction of the sodium sulphide and that black asb is obtained by directly heating sodium sulphide with calcium carbonate. 

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