95926-77-5Relevant academic research and scientific papers
Photochemistry of 1-allyl-4-aryltetrazolones in solution; Structural effects on photoproduct selectivity
Ismael, Amin,Serpa, Carlos,Cristiano, M. Lurdes S.
, p. 272 - 283 (2013/08/24)
The photochemistry of tetrazolones derived from the carbocyclic allylic alcohols cyclohex-2-enol and 3-methylcyclohex-2-enol and from the natural terpene alcohol nerol was investigated in solution with the aim of assessing the effect of solvent and of structural constraints imposed by bulky allylic moieties on photoproduct selectivity and stability. Photolysis of tetrazolones derived from nerol and cyclohex-2-enol afforded the corresponding pyrimidinones as major products through a pathway that appears to be similar to that proposed for other 1-allyl-4-phenyl-1,4-dihydro-5H-tetrazol-5-ones derived from acyclic and unhindered allylic alcohols previously investigated but photolysis of the tetrazolone derived from the bulkier 3-methylcyclohex-2-enol 4c leads to formation of a benzimidazolone, indicating that, in this case, cyclization of the biradical formed upon extrusion of N2 involves the phenyl substituent and not the allylic moiety. Theoretical calculations (DFT(B3LYP)/3-21G*) were conducted to support the interpretation of the experimental results and mechanistic proposals. Laser flash photolysis experiments were conducted with the aim of clarifying the nature of the intermediate involved in the primary photocleavage process.
Sigmatropic rearrangements in 5-allyloxytetrazoles
Frija, Luis M. T.,Reva, Igor,Ismael, Amin,Coelho, Daniela V.,Fausto, Rui,Cristiano, M. Lurdes S.
experimental part, p. 6040 - 6054 (2011/10/08)
Mechanisms of thermal isomerization of allyl tetrazolyl ethers derived from the carbocyclic allylic alcohols cyclohex-2-enol and 3-methylcyclohex-2-enol and from the natural terpene alcohol nerol were investigated. In the process of the syntheses of the t
Metal-assisted reactions. Part 25. Heterogeneous and homogeneous catalytic transfer hydrogenolysis of allyloxytetrazoles to yield alkenes or alkanes
Cristiano, M. Lurdes S.,Johnstone, Robert A. W.,Price, Peter J.
, p. 1453 - 1459 (2007/10/03)
Transfer hydrogenolysis of 5-allyloxy-1-phenyltetrazoles using either a heterogeneous or a homogeneous palladium catalyst and a hydrogen donor leads to cleavage of the allyloxy C-O bond to yield an alkane or an alkene and 1-phenyltetrazolone, depending on the catalyst used.
Photoextrusion of Nitrogen from 1,4-Dihydro-1-phenyl-5H-tetrazol-5-ones and -thiones. Benzimidazolones and Carbodiimides
Quast, Helmut,Nahr, Uwe
, p. 526 - 540 (2007/10/02)
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).
