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Descripción

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.

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Sapientia Repositório Institucional Universidade do Algarve  

Autor(es)

Ismael, A. -  Serpa, C. -  Cristiano, Maria Lurdes Santos - 

Id.: 58621891

Idioma: eng  - 

Versión: 1.0

Estado: Final

Tipo de recurso: article  - 

Tipo de Interactividad: Expositivo

Nivel de Interactividad: muy bajo

Audiencia: Estudiante  -  Profesor  -  Autor  - 

Estructura: Atomic

Coste: no

Copyright: sí

: openAccess

Requerimientos técnicos:  Browser: Any - 

Relación: [References] View Online

Fecha de contribución: 15-may-2015

Contacto:

Localización:
* Ismael, Amin; Serpa, Carlos; Cristiano, M. Lurdes S. Photochemistry of 1-allyl-4-aryltetrazolones in solution; structural effects on photoproduct selectivity, Photochemical & Photobiological Sciences, 12, 2, 272-283, 2013.
* 1474-905X

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