Thiohydroximic acids

Glucosinolates derive from amino acids by conversion to an aldoxime, R-CH=N-OH. In a not well understood process, the aldoximine is converted to a thiohydroximic acid, R-C(SH)=N-OH the introduced sulfur is likely derived from... 

Sealants obtained by curing polysulfide liquid polymers with aryl bis(nitrile oxides) possess stmctural feature of thiohydroximic acid ester. These materials exhibit poor thermal stability when heated at 60°C they soften within days and liquefy in 3 weeks. Products obtained with excess nitrile oxide degrade faster than those produced with equimolar amounts of reagents. Spectroscopic studies demonstrate that, after an initial rapid addition between nitrile oxide and thiol, a second slower reaction occurs which consumes additional nitrile oxide. Thiohydroximic acid derivatives have been shown to react with nitrile oxides at ambient temperature to form 1,2,4-oxadiazole 4-oxides and alkyl thiol. In the case of a polysulfide sealant, the rupture of a C-S bond to form the thiol involves cleavage of the polymer backbone. Continuation of the process leads to degradation of the sealant. These observations have been supported by thermal analysis studies on the poly sulfide sealants and model polymers (511). 

A copper-catalyzed aminobromination of alkene-tethered thiohydroxi-mic acids 54 provides a rapid approach to unnatural thiazoline scaffolds 55 (14OL2074). Moderate to high yields of bromothiazolines 55 are obtained with alkyl- and aryl-substituted thiohydroximic acid building blocks containing mono-, di-, and tri-substituted alkenes. The reaction provides high levels of 5-exo selectivity, and terminally mono-substituted alkenes result in predominant syn-diastereoselectivity. 

Sulfinyl cyanides N-Sulfinylimines Thiohydroxamic acids Thiohydroximic acids (esters)... 

Imino-l-sulfenic acids Oxathiol-2-ylidenimmonium salts Oxime sulfenates Sulfenyliminoesters Sulfinyl cyanides N-Sulfinylimines Thiohydroximic acids and esters... 

Aldoximes are the first intermediates of the biosynthetic pathway firmly established. They are probably formed by the reactions shown to proceed in the biosynthesis of cyanogenic glycosides (D 9.3). The first well-defined sulfur-containing intermediates are thiohydroximic acids. The most efficient source of the... 

Triethylamine Thiohydroximic acid esters from hydroximinodilorides... 

Biosynthesis of glucosinolates (reaction 17.10) starts from the corresponding amino acids, and proceeds via an oxime (I) and thiohydroximic acid (III). The intermediate reactions between... 

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