Formation of Two Bonds Four-Atom Fragment and Sulfur

2 Formation of Two Bonds Four-Atom Fragment and Sulfur 

A series of condensed 1,2,3-dithiazoles were prepared by Oakley and co-workers by the reaction of o-aminoaromatic and heterocyclic thiols and S2CI2. This approach is preferable to the common Herz reaction which fails when applied to some aromatic amines, especially to phenylenediamines (Equation 36) 1999JA969 . In some cases, less accessible SCI2 can be used 2001CJC1352 . 

The great advantage of this method is the synthesis of bis(l,2,3-dithiazoles) from diaminodithiols 1997JA12136, 1999CM164, 2000JA7602 . Reduction of radical cations formed with Ph3Sb leads to neutral heterocycles 148 and 25 as air-stable crystalline solids or to the cation 149. 

Cyclic sulfimidates can be easily oxidized to the corresponding sulfamidates. The preparation of sulfamidates from tvV-aminoalcohols can be achieved in one step without isolation of intermediate mono-A-oxides (Equation 37) 20010L405, 2002TL1915, 2005TA1583 . Yields are from moderate to high. 

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Formation of two bonds four-atom fragments and sulfur 933... 

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