19386-90-4

Upstream product

• 1521-51-3 rac-3-bromocyclohexene 
• 95926-77-5 1-(2-Cyclohexen-1-yl)-1,4-dihydro-4-phenyl-5H-tetrazol-5-on 
• 95926-78-6 4-(2-Cyclohexen-1-yl)-1,4-dihydro-1-phenyl-5H-tetrazol-5-thion 
• 95926-76-4 2-cyclohexen-1-yl-1-phenyl-1H-tetrazole-5-thiol 
• 86-93-1 1-phenyl-1H-tetrazole-5-thiol 
• 5097-82-5 5-phenyl-1H-tetrazolone 
• 95926-82-2 2-Cyclohexen-1-ylphenylcarbodiimid 

Relevant academic research and scientific papers

Photoextrusion of Nitrogen from 1,4-Dihydro-1-phenyl-5H-tetrazol-5-ones and -thiones. Benzimidazolones and Carbodiimides

Alkylation of 1-phenyltetrazolone 10a with 2-cyclohexen-1-yl bromide followed by dehydrogenation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone permits introduction of a phenyl group at N-4 of the tetrazole ring via the sequence 10a -> 10f -> 10g.The photoextrusion of molecular nitrogen from the (N-4)-substituted 1-phenyltetrazolones, 10a (hydrogen), 10b (methyl), 10d,e (propenyl), and 10g (phenyl) produces essentially quantitative yields of the corresponding benzimidazolones 14a,b,d,e,g.On irradiation of the 1-phenyltetrazolethiones 8b,f,g the carbodiimides 22b,f,g are obtained together with molecular nitrogen and sulfur, while 8a affords phenylcyanamide (25).In contrast to the thermolysis, which is known to give 2-(methylamino)benzothiazole (21b), photolysis of the (phenylimino)-1,2,3,4-thiatriazole 24, an isomer of methylphenyltetrazolethione 8b, also yields molecular nitrogen, sulfur, and methylphenylcarbodiimide (22b).