1.3- Dithiolium - from 2- amino

Cyanogen chloride has so far been reacted, always with very good yields, with a series of ethane-1,2-diols and ethane-1,2-dithiols, as well as with benzene-1,2-dithiol however, it has not yet been reacted with the simple ethylene-1,2-dithiol, which now offers further preparative possibilities in view of the new syntheses mentioned earlier. Similar 2-amino substituted 1,3-dithiolium derivatives have been synthesized by Sundholm and Smith starting from 2,3-dichloro-... 

Amino-l,2-dithiolium salts are obtained from either / -oxocarbox-amides or ) -oxocarbonitriles by reaction with phosphorus penta-sulfide, followed by addition of perchloric acid (Scheme 6). These cations, which may also be considered as iminium salts, are deprotonated to the corresponding l,2-dithiol-3-imine by ammonia. ... 

Amino-dithioacrylic-esters 22 prepared from 3-alkylthio-l,2-dithiolium salts with primary amines reacted by oxidative S,N-ring closure with I2/EtOH... 

There are general reviews on heterocyclic syntheses by cycloaddition reactions of isocyanates and on the use of heterocyclic cations in preparative organic chemistry. More specific topics are 5-hydroxymethylfuran-2-carb-aldehyde, isobenzofurans and related ort/io-quinonoid systems, the conversion of 2//-cyclohepta[Zj] furan-2-one (1) into derivatives of azulene, the synthesis of indoles from o-alkylphenyl isocyanides, and abnormal Fischer indolization reactions of o-methoxyphenylhydrazones. Two reviews on isoindoles have appeared and a lecture on highly conducting charge-transfer complexes that are based on heterocyclic selenium and tellurium donors has been reprinted.Recent advances in the chemistry of imidazole and in the use of nitro-imidazoles as radiosensitizers have been summarized. There have been reviews on benzimidazole A -oxides and on dihydrobenzimidazoles, benzimidazolones, benzimidazolethiones, and related compounds. Other topics are synthetic applications of 1,3-dithiolium and 1,3-oxathiolium salts and of isoxazoles, the chemistry of benzisoxazoles, 2-amino-oxazoles, 5-oxazolones (2), furoxans, benzofuroxans, and related systems, the synthesis of five-membered meso-ionic compounds, and tetrazoles. ... 

Perchloric acid 1,3-Dithiolium salts from 2-amino-l,3-dithioles... 

Dithiolium salts, e.g. (126), can be made from the dithioester (125) by reaction with acetic anhydride in polar solvents the meso-ionic 1,3-dithiolium-4-olate (127) is readily produced. If dithiocarbamates are used as starting materials, then 2-amino-l,3-dithiolium-4-olates are formed. ... 

Reactions of 2-methylthio-l,3-dithiolium salts with sodium azide have been investigated the products include 3-methylthio-l,4,2-dithiazines and sul-phenimides (47), from which 2-amino-1,3-dithiolium salts and other related compounds can be prepared. 

---