Hypervalent Heterocycles

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

5 Scopus citations


This chapter provides an overview of recent literature on heterocyclic molecules incorporating an atom of a hypervalent main-group element. The term "hypervalent" has been suggested for derivatives of main-group elements with more than eight valence electrons, and the concept of hypervalency is commonly used in synthetic works despite criticism from theoretical chemists. Typical hypervalent heterocycles include polycoordinated 10-electron or 12-electron centers with distorted trigonal-bipyramidal or pseudooctahedral geometry, respectively. In general, heterocyclic compounds of elements with double bonds are not classified as hypervalent molecules because of the ylidic, zwitterionic nature of such bonds resulting in the classical 8-electron species. Despite the lack of aromatic conjugation, hypervalent heterocycles often have a considerably higher thermal stability compared to their acyclic analogs, which is especially. important in the chemistry of polyvalent bromine and iodine. This review is centered mainly on hypervalent heterocyclic derivatives of nonmetal main-group elements, such as, boron, silicon, phosphorus, sulfur, selenium, bromine, and iodine, with emphasis on structural and synthetic aspects of their chemistry.

Original languageEnglish (US)
Title of host publicationHeterocyclic Chemistry in the 21st Century A Tribute to Alan Katritzky, 2016
EditorsEric F.V. Scriven, Christopher A. Ramsden
PublisherAcademic Press Inc.
Number of pages23
ISBN (Print)9780128046951
StatePublished - 2016

Publication series

NameAdvances in Heterocyclic Chemistry
ISSN (Print)0065-2725

Bibliographical note

Copyright 2018 Elsevier B.V., All rights reserved.


  • Benziodoxoles
  • Hypervalency
  • Hypervalent
  • Hypervalent boron
  • Hypervalent bromine
  • Hypervalent heterocycles
  • Hypervalent iodine
  • Hypervalent silicon
  • Hypervalent sulfur
  • Iodine heterocycles


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