Jump to main content
Jump to site search

Issue 45, 2019
Previous Article Next Article

Structure–property-reactivity studies on dithiaphospholes

Author affiliations


The reaction of either toluene-3,4-dithiol or benzene dithiol with phosphorus(III) trihalides generates the corresponding benzo-fused 1,3,2-dithiaphospholes, RC6H3S2PX (R = Me (1), R = H (2); X = Cl, Br, I). The P-chloro-dithiaphospholes undergo: (a) halogen abstraction reactions with Lewis acids forming phosphenium cations; (b) substitution with LiHMDS base and; (c) reduction chemistry with sodium metal to generate the P–P σ-bonded dimer, (RC6H3S2P)2. Reduction catalysis of aldehydes with pinacolborane using dithiaphospholes is compared with their dioxaphosphole and diazaphosphole counterparts as pre-catalysts, revealing interesting differences in the reactivity of this series of compounds.

Graphical abstract: Structure–property-reactivity studies on dithiaphospholes

Back to tab navigation

Supplementary files

Article information

04 Sep 2019
24 Sep 2019
First published
04 Nov 2019

This article is Open Access

Dalton Trans., 2019,48, 16922-16935
Article type

Structure–property-reactivity studies on dithiaphospholes

D. M. C. Ould, T. T. P. Tran, J. M. Rawson and R. L. Melen, Dalton Trans., 2019, 48, 16922
DOI: 10.1039/C9DT03577J

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material.

Reproduced material should be attributed as follows:

  • For reproduction of material from NJC:
    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
  • For reproduction of material from PCCP:
    [Original citation] - Published by the PCCP Owner Societies.
  • For reproduction of material from PPS:
    [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
  • For reproduction of material from all other RSC journals:
    [Original citation] - Published by The Royal Society of Chemistry.

Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Social activity

Search articles by author