Reversible cyclisation of a sulfonated arylazo compound containing an o-acetylamino substituent

David I. Gibson; John A. Parkinson; Anita C. Jones; Warren J. Ebenezer; Michael G. Hutchings

doi:10.1016/j.tetlet.2007.12.081

Reversible cyclisation of a sulfonated arylazo compound containing an o-acetylamino substituent

David I. Gibson
, John A. Parkinson
, Anita C. Jones
, Warren J. Ebenezer
, Michael G. Hutchings

Research output: Contribution to journal › Article › peer-review

Abstract

A sulfonated o-acetylamino arylazo compound unexpectedly cyclised to a cationic benzo-1,2,4-triazinium species under thermal or acid conditions, reversible with base. The same substrate underwent trans to cis-azo photoisomerisation, observable by NMR spectroscopy, under steady state laser irradiation conditions. (c) 2007 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	1388-1392
Number of pages	5
Journal	Tetrahedron Letters
Volume	49
Issue number	8
DOIs	https://doi.org/10.1016/j.tetlet.2007.12.081
Publication status	Published - 18 Feb 2008

Keywords / Materials (for Non-textual outputs)

arylazo
benzo-1,2,4-triazine
cyclisation
photoisomerism
NMR-SPECTROSCOPY
N-15 NMR

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10.1016/j.tetlet.2007.12.081

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title = "Reversible cyclisation of a sulfonated arylazo compound containing an o-acetylamino substituent",

abstract = "A sulfonated o-acetylamino arylazo compound unexpectedly cyclised to a cationic benzo-1,2,4-triazinium species under thermal or acid conditions, reversible with base. The same substrate underwent trans to cis-azo photoisomerisation, observable by NMR spectroscopy, under steady state laser irradiation conditions. (c) 2007 Elsevier Ltd. All rights reserved.",

keywords = "arylazo, benzo-1,2,4-triazine, cyclisation, photoisomerism, NMR-SPECTROSCOPY, N-15 NMR",

author = "Gibson, \{David I.\} and Parkinson, \{John A.\} and Jones, \{Anita C.\} and Ebenezer, \{Warren J.\} and Hutchings, \{Michael G.\}",

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doi = "10.1016/j.tetlet.2007.12.081",

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T1 - Reversible cyclisation of a sulfonated arylazo compound containing an o-acetylamino substituent

AU - Gibson, David I.

AU - Parkinson, John A.

AU - Jones, Anita C.

AU - Ebenezer, Warren J.

AU - Hutchings, Michael G.

PY - 2008/2/18

Y1 - 2008/2/18

N2 - A sulfonated o-acetylamino arylazo compound unexpectedly cyclised to a cationic benzo-1,2,4-triazinium species under thermal or acid conditions, reversible with base. The same substrate underwent trans to cis-azo photoisomerisation, observable by NMR spectroscopy, under steady state laser irradiation conditions. (c) 2007 Elsevier Ltd. All rights reserved.

AB - A sulfonated o-acetylamino arylazo compound unexpectedly cyclised to a cationic benzo-1,2,4-triazinium species under thermal or acid conditions, reversible with base. The same substrate underwent trans to cis-azo photoisomerisation, observable by NMR spectroscopy, under steady state laser irradiation conditions. (c) 2007 Elsevier Ltd. All rights reserved.

KW - arylazo

KW - benzo-1,2,4-triazine

KW - cyclisation

KW - photoisomerism

KW - NMR-SPECTROSCOPY

KW - N-15 NMR

UR - https://www.scopus.com/pages/publications/38349190656

U2 - 10.1016/j.tetlet.2007.12.081

DO - 10.1016/j.tetlet.2007.12.081

M3 - Article

SN - 0040-4039

VL - 49

SP - 1388

EP - 1392

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 8

ER -

Reversible cyclisation of a sulfonated arylazo compound containing an o-acetylamino substituent

Abstract

Keywords / Materials (for Non-textual outputs)

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