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Molecules 2017, 22(10), 1687; doi:10.3390/molecules22101687

Phosphorus-Sulfur Heterocycles Incorporating an O-P(S)-O or O-P(S)-S-S-P(S)-O Scaffold: One-Pot Synthesis and Crystal Structure Study

EaStCHEM School of Chemistry, University of St Andrews, Fife KY16 9ST, UK
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Received: 7 September 2017 / Accepted: 4 October 2017 / Published: 10 October 2017
(This article belongs to the Special Issue Main Group Elements in Synthesis)
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Abstract

A new one-pot preparative route was developed to synthesize novel organophosphorus-sulfur heterocycles via the reaction of the four-membered ring thionation reagent [2,4-diferrocenyl-1,3,2,4-diathiadiphosphetane 2,4-disulfide (FcLR, a ferrocene analogue of Lawesson’s reagent)] and alkenyl/aryl-diols and I2 (or SOCl2) in the presence of triethylamine. Therefore, a series of five- to ten-membered heterocycles bearing an O-P(S)-O or an O-P(S)-S-S-P(S)-O linkage were synthesized. The synthesis features a novel application of the multicomponent reaction, providing an efficient and environmentally benign method for the preparation of the unusual phosphorus-sulfur heterocycles. Seven representative X-ray structures confirm the formation of these heterocycles. View Full-Text
Keywords: 2,4-Diferrocenyl-1,3,2,4-diathiadiphosphetane 2,4-disulfide; diols; one-pot reaction; iodine oxidation; phosphorus-sulfur heterocycles 2,4-Diferrocenyl-1,3,2,4-diathiadiphosphetane 2,4-disulfide; diols; one-pot reaction; iodine oxidation; phosphorus-sulfur heterocycles
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Hua, G.; Davidson, K.; Cordes, D.B.; Du, J.; Slawin, A.M.Z.; Woollins, J.D. Phosphorus-Sulfur Heterocycles Incorporating an O-P(S)-O or O-P(S)-S-S-P(S)-O Scaffold: One-Pot Synthesis and Crystal Structure Study. Molecules 2017, 22, 1687.

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