Iodine Heterocycles

Research output: Chapter in Book/Report/Conference proceedingConference contribution

11 Scopus citations

Abstract

This chapter provides the first comprehensive review covering all main aspects of the chemistry of iodine heterocycles including preparation, structure, and synthetic applications. The most important and practically useful polyvalent iodine heterocycles have a five-membered ring, although several examples of three-membered, four-membered, and six-membered heterocycles with an iodine(III) or iodine(V) atom in the ring are also known. In general, iodine is not capable of forming conjugated cyclic systems with aromatic stabilization because of the large atom size and the semi-ionic nature of the hypervalent I-C, I-N, and I-O bonds. Despite the lack of aromatic conjugation, the five-membered heterocyclic iodine compounds (benziodoxoles and benziododazoles) have a considerably higher thermal stability compared to their acyclic analogs, which has made possible the preparation and isolation of iodine-substituted derivatives, such as bromobenziodoxoles, tosyloxybenziodoxoles, alkylperoxybenziodoxoles, azidobenziodoxoles, cyanobenziodoxoles, amidobenziodoxoles, alkynylbenziodoxoles, and trifluoromethylbenziodoxoles. Derivatives of benziodoxoles have found wide practical applications as oxidants and reagents for atom-transfer reactions in organic synthesis.

Original languageEnglish (US)
Title of host publicationAdvances in Heterocyclic Chemistry, 2015
EditorsEric F.V. Scriven, Christopher A. Ramsden
PublisherAcademic Press Inc.
Pages1-91
Number of pages91
ISBN (Print)9780128021293
DOIs
StatePublished - 2015

Publication series

NameAdvances in Heterocyclic Chemistry
Volume115
ISSN (Print)0065-2725

Bibliographical note

Publisher Copyright:
© 2015 Elsevier Inc.

Keywords

  • 2-Iodoxybenzoic acid
  • Benziodoxoles
  • Cyclic iodonium
  • Dess-Martin periodinane
  • Hypervalent iodine
  • Iodine
  • Iodine heterocycles

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