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Peroxide Decompositions, II: Dioxetans

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Chemiluminescence in Organic Chemistry

Part of the book series: Reactivity and Structure: Concepts in Organic Chemistry ((REACTIVITY,volume 23))

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Abstract

Like many reactive molecules with slightly unconventional arrangements of bonds — usually involving a high degree of ring strain — dioxetans had been erroneously identified [1] long before their actual synthesis [2]. Thus there was a fair degree of resistance to their use in rationalising chemiluminescence mechanism. Although some circumstantial evidence [3] for their involvement had appeared before 1969, the application of orbital symmetry rules [4, 5] in an attempt to explain the formation of excited states provoked attempts to study them. Shortly afterwards the first synthesis [2] of an isolable dioxetan showed that although unstable, they were certainly not so reactive as to prevent manipulation. They were indeed chemiluminescent. Since then over one hundred dioxetans of varying stability have been synthesised. Compounds with half lives from minutes to thousands of years at room temperature have been obtained [6].

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Authors and Affiliations

  1. Institut für Organische Chemie, Technische Universität Clausthal, D-3392, Clausthal-Zellerfeld, Germany

    Professor Dr. Karl-Dietrich Gundermann

  2. The School of Chemistry and Molecular Sciences, The University of Sussex, BN1 9QJ, Falmer, Brighton, UK

    Professor Frank McCapra

Authors
  1. Professor Dr. Karl-Dietrich Gundermann
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  2. Professor Frank McCapra
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© 1987 Springer-Verlag Berlin Heidelberg

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Gundermann, KD., McCapra, F. (1987). Peroxide Decompositions, II: Dioxetans. In: Chemiluminescence in Organic Chemistry. Reactivity and Structure: Concepts in Organic Chemistry, vol 23. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-71645-4_5

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  • DOI: https://doi.org/10.1007/978-3-642-71645-4_5

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-71647-8

  • Online ISBN: 978-3-642-71645-4

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