Tetrazole-5-thiolates

It has been shown that 5-aminothiatriazoles (13) react with sodium hydroxide <1895CB74,57CJC832, 67JOC3580) to give tetrazole-5-thiolate (98). Thus Lieber et al. described how treatment with aqueous sodium hydroxide gave rise to a mixture of tetrazole (98) (path (a)) and isocyanate and azide (path (b)) (Scheme 17) <57CJC832>. 

Triorganotin derivatives of 1 -phenyl- 17/-tetrazole-5-thiol also tend to self-assemble in the solid state359-361. For example, tribenzyltin 1 -phenyl-1H-tetrazole-5-thiolate, Bz3SnSCN4Ph (161), forms a linear coordination polymer with intermolecular Sn—N distances of 2.559(12) and 2.676(10) A and intramolecular Sn—S distances of 2.565(4) A359, whereas trimethyltin 1-phenyl-177-tetrazole-5-thiolate, Me3SnSCN4Ph360, self-assembles to give trimers. 

Triraethyltin(IV) l-phenyl-17/-tetrazole-5-thiolate, Me3SnSCN4Ph, is self-assembled into trimeric supermolecules, 121. The primary bond is between tin and... 

The triorganotin(IV) 1-phenyl-17/-tetrazole-5-thiolates, R3SnSCN4R, (R = Me, Bu, Ph, R = Me, Ph) were found to be monomeric in solution, but spectroscopic data suggest that all are self-assembled in the solid state [293]. 

Substituted tetrazoles reacting in the mass spectrometer with acyl ions afforded 2,5-disubstituted 1,3,4-oxadiazoles with nitrogen loss. Tandem mass spectrometry allowed for the collision-induced dissociation of the products. Chemical ionization was the better method to make the transformation. A scheme for the transformation of 5-substituted tetrazoles into 2,5-disubstituted 1,3,4-oxadiazoles was proposed (Scheme 1) <2001JMP1069>. The fragmentation patterns of monocyclic l,3,4-oxadiazolium-2-thiolates have been proposed by Ollis and Ramsden <1974J(P1)645>. 

Azide ion has been shown to be an effective trap for a Beckmann intermediate. Treatment of acetophenone oxime with thionyl cloride in the presence of hydrazoic acid gave tetrazole (37), as shown in equation (23). Thiolates participate efficiendy in Beckmann reactions, and the sulW nucleophile may be incorporated into a Lewis acidic reagent, as demonstrated in equation (24). ... 

Recent studies of mesoionic tetrazoles have centered mainly on 2,3-diphenyl-2//-tetrazolium-5-thiolate (72), also known as dehydro-dithizone, and on the synthesis of some new tetrazoles. The structure of the product formed when dithizone (207) was oxidized with a number of oxidizing agents was correctly formulated as 72 by Ogilvie and Corwin446 and has since been confirmed by X-ray analysis."3,134... 

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