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Pure and Applied Chemistry

The Scientific Journal of IUPAC

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Volume 89, Issue 3

Issues

Sterically protected organophosphorus compounds of unusual structures

Masaaki Yoshifuji
  • Corresponding author
  • Department of Chemistry, Graduate School of Science, Tohoku University, 6-3 Aramaki Aza-Aoba, Aoba, Sendai, Miyagi, 980-0845, Japan
  • Department of Chemistry, The University of Alabama, Tuscaloosa, Alabama, AL 35487-0336, USA
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Published Online: 2017-02-07 | DOI: https://doi.org/10.1515/pac-2016-1029

Abstract

The character of bis(2,4,6-tri-tert-butylphenyl)diphosphene is described experimentally and theoretically. The diphosphene is stabilized by steric protection and the structure can be characterized by spectroscopic as well as crystallographic analyses. Theoretical calculation on the diphosphene strongly suggests that the P=P bond is an isolated double bond and that the P–C bonds are single covalent bond. The reactivity has been investigated including photolysis, oxidation, sulfurization, selenation, transition-metal complex formation, and carbene addition. Plausible mechanistic scheme for the reaction of the diphosphene with 3,4,5,6-tetrachlorocyclohexa-3,5-diene-1,2-dione (or tetrachloro-o-benzoquinone) to a pentavalent spiro product is discussed based on the product analysis.

Keywords: diphosphene; ICPC-21; low coordination; steric protection

Article note:

A collection of invited papers based on presentations at the 21st International Conference on Phosphorous Chemistry (ICPC-21) held in Kazan, Russia, 5–10 June 2016.

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About the article

Published Online: 2017-02-07

Published in Print: 2017-03-01


Citation Information: Pure and Applied Chemistry, Volume 89, Issue 3, Pages 281–286, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1515/pac-2016-1029.

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