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Structure-property-reactivity studies on dithiaphospholes

Ould, Darren M. C., Tran, Thao T. P., Rawson, Jeremy M. and Melen, Rebecca L. 2019. Structure-property-reactivity studies on dithiaphospholes. Dalton Transactions 48 (45) , pp. 16922-16935. 10.1039/C9DT03577J

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Abstract

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 precatalysts, revealing interesting differences in the reactivity of this series of compounds.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Cardiff Catalysis Institute (CCI)
Publisher: Royal Society of Chemistry
ISSN: 1477-9226
Funders: EPSRC
Date of First Compliant Deposit: 8 November 2019
Date of Acceptance: 24 September 2019
Last Modified: 13 Dec 2019 15:49
URI: http://orca.cf.ac.uk/id/eprint/126664

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