Organic and Biomolecular Chemistry, volume 6, issue 6, pages 1046

Photochemistry of 5-allyloxy-tetrazoles: steady-state and laser flash photolysis study

Luı́s M.T Frija ^{1, 2}

Vladimir.I Makarov ³

Carlos Serpa ²

Igor Reva ²

Rui Fausto ²

Maria L. S. Cristiano ¹

Hide authors affiliations Show authors affiliations: 3 affiliations

Department of Chemistry, Biochemistry and Pharmacy, F.C.T. and CCMAR, University of Algarve, 8005-039 Faro, Portugal |

Department of Chemistry, F.C.T., University of Coimbra, R. Larga, P-3004-535 Coimbra, Portugal |

Department of Chemistry, Biochemistry and Pharmacy, F.C.T and CIQA, University of Algarve, 8005-039 Faro, Portugal |

Publication type: Journal Article

Publication date: 2008-02-14

Royal Society of Chemistry (RSC)

Journal: Organic and Biomolecular Chemistry

Quartile SCImago

Quartile WOS

Impact factor: 3.2

ISSN: 14770520, 14770539

DOI: 10.1039/b718104c

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Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Abstract

The photochemistry of three 5-allyloxy-tetrazoles, in methanol, acetonitrile and cyclohexane was studied by product analysis and laser flash photolysis. The exclusive primary photochemical process identified was molecular nitrogen elimination, with formation of 1,3-oxazines. These compounds were isolated in reasonable yields by column chromatography on silica gel and were fully characterized. DFT(B3LYP)/6-31G(d,p) calculations predict that these 1,3-oxazines can adopt two tautomeric forms (i) with the NH group acting as a bridge connecting the oxazine and phenyl rings and (ii) with the -N=bridge and the proton shifted to the oxazine ring. Both tautomeric forms are relevant in the photolysis of oxazines in solution. Secondary reactions were observed, leading to the production of phenyl vinyl-hydrazines, enamines, aniline and phenyl-isocyanate. Transient absorption, detected by laser flash photolysis, is attributed to the formation of triplet 1,3-biradicals generated from the excited 5-allyloxy-tetrazoles. The 1,3-biradicals are converted to 1,6-biradicals by proton transfer, which, after intersystem crossing, decay to generate the products. Solvent effects on the photoproduct distribution and rate of decomposition are negligible.

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European Journal of Organic Chemistry	European Journal of Organic Chemistry, 1, 4.35% European Journal of Organic Chemistry 1 publication, 4.35%
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Citations by publishers

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Elsevier	Elsevier, 9, 39.13% Elsevier 9 publications, 39.13%
Multidisciplinary Digital Publishing Institute (MDPI)	Multidisciplinary Digital Publishing Institute (MDPI), 3, 13.04% Multidisciplinary Digital Publishing Institute (MDPI) 3 publications, 13.04%
Wiley	Wiley, 3, 13.04% Wiley 3 publications, 13.04%
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American Chemical Society (ACS)	American Chemical Society (ACS), 2, 8.7% American Chemical Society (ACS) 2 publications, 8.7%
American Institute of Physics (AIP)	American Institute of Physics (AIP), 1, 4.35% American Institute of Physics (AIP) 1 publication, 4.35%
Springer Nature	Springer Nature, 1, 4.35% Springer Nature 1 publication, 4.35%
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii	Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii, 1, 4.35% Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii 1 publication, 4.35%
	1 2 3 4 5 6 7 8 9

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Frija L. M. et al. Photochemistry of 5-allyloxy-tetrazoles: steady-state and laser flash photolysis study // Organic and Biomolecular Chemistry. 2008. Vol. 6. No. 6. p. 1046.

GOST all authors (up to 50) Copy

Frija L. M., Makarov V., Serpa C., Reva I., Fausto R., Cristiano M. L. S. Photochemistry of 5-allyloxy-tetrazoles: steady-state and laser flash photolysis study // Organic and Biomolecular Chemistry. 2008. Vol. 6. No. 6. p. 1046.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1039/b718104c

UR - https://doi.org/10.1039/b718104c

TI - Photochemistry of 5-allyloxy-tetrazoles: steady-state and laser flash photolysis study

T2 - Organic and Biomolecular Chemistry

AU - Frija, Luı́s M.T

AU - Makarov, Vladimir.I

AU - Serpa, Carlos

AU - Reva, Igor

AU - Fausto, Rui

AU - Cristiano, Maria L. S.

PY - 2008

DA - 2008/02/14 00:00:00

PB - Royal Society of Chemistry (RSC)

SP - 1046

IS - 6

VL - 6

SN - 1477-0520

SN - 1477-0539

ER -

BibTex |

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BibTex Copy

@article{2008_Frija,

author = {Luı́s M.T Frija and Vladimir.I Makarov and Carlos Serpa and Igor Reva and Rui Fausto and Maria L. S. Cristiano},

title = {Photochemistry of 5-allyloxy-tetrazoles: steady-state and laser flash photolysis study},

journal = {Organic and Biomolecular Chemistry},

year = {2008},

volume = {6},

publisher = {Royal Society of Chemistry (RSC)},

month = {feb},

url = {https://doi.org/10.1039/b718104c},

number = {6},

pages = {1046},

doi = {10.1039/b718104c}

}

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Frija, Luı́s M.T, et al. “Photochemistry of 5-allyloxy-tetrazoles: steady-state and laser flash photolysis study.” Organic and Biomolecular Chemistry, vol. 6, no. 6, Feb. 2008, p. 1046. https://doi.org/10.1039/b718104c.

Found error?

Publisher

Royal Society of Chemistry (RSC)

Journal

Organic and Biomolecular Chemistry

Quartile SCImago

Quartile WOS

Impact factor

3.2

ISSN

14770520 (Print)
14770539 (Electronic)

Profiles

Fausto, Rui L