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Ueta Y, Mikami K, Ito S. Access to Air-Stable 1,3-Diphosphacyclobutane-2,4-diyls by an Arylation Reaction with Arynes. Angew Chem Int Ed Engl. 2016;55(26):7525-9doi: 10.1002/anie.201601907.
Ueta, Y., Mikami, K., & Ito, S. (2016). Access to Air-Stable 1,3-Diphosphacyclobutane-2,4-diyls by an Arylation Reaction with Arynes. Angewandte Chemie (International ed. in English), 55(26), 7525-9. https://doi.org/10.1002/anie.201601907
Ueta, Yasuhiro, et al. "Access to Air-Stable 1,3-Diphosphacyclobutane-2,4-diyls by an Arylation Reaction with Arynes." Angewandte Chemie (International ed. in English) vol. 55,26 (2016): 7525-9. doi: https://doi.org/10.1002/anie.201601907
Ueta Y, Mikami K, Ito S. Access to Air-Stable 1,3-Diphosphacyclobutane-2,4-diyls by an Arylation Reaction with Arynes. Angew Chem Int Ed Engl. 2016 Jun 20;55(26):7525-9. doi: 10.1002/anie.201601907. Epub 2016 May 02. PMID: 27135439.
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Angew Chem Int Ed Engl. 2016 Jun 20;55(26):7525-9. doi: 10.1002/anie.201601907. Epub 2016 May 02.

Access to Air-Stable 1,3-Diphosphacyclobutane-2,4-diyls by an Arylation Reaction with Arynes.

Angewandte Chemie (International ed. in English)

Yasuhiro Ueta, Koichi Mikami, Shigekazu Ito

Affiliations

  1. School of Materials and Chemical Technology, Department of Chemical Science and Engineering, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro, Tokyo, 152-8552, Japan.
  2. School of Materials and Chemical Technology, Department of Chemical Science and Engineering, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro, Tokyo, 152-8552, Japan. [email protected].

PMID: 27135439 DOI: 10.1002/anie.201601907

Abstract

Tuning of the physicochemical properties of the 1,3-diphosphacyclobutane-2,4-diyl unit is attractive in view of materials applications. The use of arynes is shown to be effective for installing relatively electron rich aryl substituents into the open-shell singlet P-heterocyclic system. Treatment of the sterically encumbered 1,3-diphosphacyclobuten-4-yl anion with ortho-silylated aryl triflates in the presence of fluoride under appropriate conditions afforded the corresponding 1-aryl 1,3-diphosphacyclobutane-2,4-diyls. The air-stable open-shell singlet P-heterocycles exhibit considerable electron-donating character, and the aromatic substituent influences the open-shell character, which is thought to be related to the property of p-type semiconductivity. The P-arylated 1,3-diphosphacyclobutane-2,4-diyl systems can be further utilized as detectors of hydrogen fluoride (HF), which causes a remarkable change in their photoabsorption properties.

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: arynes; fluorine; heterocycles; phosphorus; radicals

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