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Diethyl (iodoethynyl)phosphonate and (iodoethynyl)diphenylphosphane oxide: crystal structures and some cycloaddition reactions

  • Aline Marian and Gerhard Maas ORCID logo EMAIL logo

Abstract

The title compounds are difunctionalized acetylenic building blocks, which can serve as electrophilic dienophiles and dipolarophiles in [4+2] and azide-iodoalkyne [3+2] cycloaddition reactions, which, however, require strong thermal activation. In their crystal structures, they are self-complementary tectons, which are arranged in polymeric chains maintained by very short intermolecular Csp–I···O=P halogen bonds.


Corresponding author: Gerhard Maas, Institute of Organic Chemistry I, Ulm University, Albert-Einstein-Allee 11, D-89081 Ulm, Germany, E-mail:

Acknowledgements

We thank B. Müller (Institute of Inorganic Chemistry II) for the X-ray diffraction data collection and Dr. M. Wunderlin for the mass spectra.

  1. Author contribution: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: Ulm University.

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

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Supplementary material

The online version of this article offers supplementary material (https://doi.org/10.1515/znb-2020-0047).

Received: 2020-04-03
Accepted: 2020-05-12
Published Online: 2020-06-30
Published in Print: 2020-08-27

© 2020 Walter de Gruyter GmbH, Berlin/Boston

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