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

Guoxiong Hua; Kate Davidson; David B. Cordes; Junyi Du; Alexandra M. Z. Slawin; J. Derek Woollins

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

Guoxiong Hua, Kate Davidson, David B. Cordes, Junyi Du, Alexandra M. Z. Slawin, J. Derek Woollins

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Article number	1687
Number of pages	14
Journal	Molecules
Volume	22
Issue number	10
DOIs	https://doi.org/10.3390/molecules22101687
Publication status	Published - 10 Oct 2017

Keywords

2,4-Diferrocenyl-1,3,2,4-diathiadiphosphetane 2,4-disulfide
Diols
One-pot reaction
Iodine oxidation
Phosphorus-sulfur heterocycles

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© 2017 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
Final published version, 3.14 MBLicence: CC BY

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 (dataset)
Hua, G. (Creator), Davidson, K. (Creator), Cordes, D. B. (Creator), Du, J. (Creator), Slawin, A. M. Z. (Creator) & Woollins, J. D. (Creator), Cambridge Crystallographic Data Centre, 5 Sept 2017
https://dx.doi.org/10.5517/ccdc.csd.cc1psj44 and 6 more links, https://dx.doi.org/10.5517/ccdc.csd.cc1psj55, https://dx.doi.org/10.5517/ccdc.csd.cc1psj66, https://dx.doi.org/10.5517/ccdc.csd.cc1psj77, https://dx.doi.org/10.5517/ccdc.csd.cc1psj88, https://dx.doi.org/10.5517/ccdc.csd.cc1psj99, https://dx.doi.org/10.5517/ccdc.csd.cc1psjbb (show fewer)
Dataset

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@article{8ad4c897058347efb74cca7f5400ef14,

title = "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",

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{\textquoteright}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.",

keywords = "2,4-Diferrocenyl-1,3,2,4-diathiadiphosphetane 2,4-disulfide, Diols, One-pot reaction, Iodine oxidation, Phosphorus-sulfur heterocycles",

author = "Guoxiong Hua and Kate Davidson and Cordes, {David B.} and Junyi Du and Slawin, {Alexandra M. Z.} and Woollins, {J. Derek}",

note = "The authors are grateful to the University of St Andrews for financial support.",

year = "2017",

month = oct,

day = "10",

doi = "10.3390/molecules22101687",

language = "English",

volume = "22",

journal = "Molecules",

issn = "1420-3049",

publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",

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TY - JOUR

T1 - Phosphorus-sulfur heterocycles incorporating an O-P(S)-O or O-P(S)-S-S-P(S)-O scaffold

T2 - one-pot synthesis and crystal structure study

AU - Hua, Guoxiong

AU - Davidson, Kate

AU - Cordes, David B.

AU - Du, Junyi

AU - Slawin, Alexandra M. Z.

AU - Woollins, J. Derek

N1 - The authors are grateful to the University of St Andrews for financial support.

PY - 2017/10/10

Y1 - 2017/10/10

N2 - 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.

AB - 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.

KW - 2,4-Diferrocenyl-1,3,2,4-diathiadiphosphetane 2,4-disulfide

KW - Diols

KW - One-pot reaction

KW - Iodine oxidation

KW - Phosphorus-sulfur heterocycles

U2 - 10.3390/molecules22101687

DO - 10.3390/molecules22101687

M3 - Article

SN - 1420-3049

VL - 22

JO - Molecules

JF - Molecules

IS - 10

M1 - 1687

ER -

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

Abstract

Keywords

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Datasets

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 (dataset)

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