Hexadehydro Diels-Alder (HDDA) Route to Arynes and Related Chemistry

Rachel N. Voss, Thomas R. Hoye

Research output: Chapter in Book/Report/Conference proceedingChapter

2 Scopus citations


The title reaction, first revealed in 1997, has seen expansive growth since a report in 2012 demonstrated its potential as a general strategy for creating reactive benzyne intermediates from simple triyne precursors. In contrast to the presence of reagents (and their byproducts) used in the vast majority of the classical methods for aryne formation seen in the Chapters 1, 8 and 9 in this Handbook, the simple thermal reaction conditions used for hexadehydro Diels-Alder (HDDA)-benzyne generation are pristine. This often allows for new types of aryne-trapping reactions and for new mechanistic insights to be revealed. Examples of these can be seen in the selections presented in this chapter. Guidelines for designing new HDDA studies, from both strategic and experimental design perspectives, are presented in the last several pages.

Original languageEnglish (US)
Title of host publicationModern Aryne Chemistry
Number of pages38
ISBN (Electronic)9783527823086
ISBN (Print)9783527346462
StatePublished - Jan 1 2021
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2021 WILEY-VCH GmbH, Boschstr. 12, 69469 Weinheim, Germany.


  • design strategies
  • experimental guidelines
  • new aryne-trapping reactions
  • new mechanistic insights


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