Issue 45, 2019

Structure–property-reactivity studies on dithiaphospholes


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

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Article information

Article type
04 Sep 2019
24 Sep 2019
First published
04 Nov 2019
This article is Open Access
Creative Commons BY license

Dalton Trans., 2019,48, 16922-16935

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

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