Application of four-membered ring chalcogenation reagents to the synthesis of new phosphorus-chalcogen heterocycles

Guoxiong Hua; David Bradford Cordes; Alexandra Martha Zoya Slawin; J Derek Woollins

doi:10.3998/ark.5550190.p009.807

Application of four-membered ring chalcogenation reagents to the synthesis of new phosphorus-chalcogen heterocycles

Guoxiong Hua
, David Bradford Cordes
, Alexandra Martha Zoya Slawin
, J Derek Woollins

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

Abstract

The reaction of four-membered ring chalcogenation reagents such as Lawesson’s reagent, 2,4-diferrocenyl-1,3,2,4-diathiadiphosphetane 2,4-disulfide (the ferrocene analogy of Lawesson’s reagent) and Woollins’ reagent with alkyl- or aryl-dithiols in refluxing toluene gave a series of five- to seven-membered organo-phosphorus-chalcogen heterocycles in 24% to 87% yields. Five representative X-ray structures confirm the formation of these five- to seven-membered heterocycles.

Original language	English
Pages (from-to)	9-20
Journal	ARKIVOC
Volume	2017
Issue number	2
Early online date	29 Aug 2016
DOIs	https://doi.org/10.3998/ark.5550190.p009.807
Publication status	E-pub ahead of print - 29 Aug 2016

Keywords

Lawesson’s reagent
Woollins’ reagent
X-ray structure
Phosphorus‐chalcogen heterocycles
Chalcogenation
Dithiols

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Woollins_2016_ARKIVOC_Application_FinalPublishedVersion
© ARKAT USA, Inc. This work is made available online with permission from the publisher. This is the final published version of the work, which was originally published at: https://dx.doi.org/10.3998/ark.5550190.p009.807
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Application of four-membered ring chalcogenation reagents to the synthesis of new phosphorus-chalcogen heterocycles (dataset)
Hua, G. (Creator), Cordes, D. B. (Creator), Slawin, A. M. Z. (Creator) & Woollins, J. D. (Creator), Cambridge Crystallographic Data Centre, 2016
https://dx.doi.org/10.5517/ccdc.csd.cc1m5njz and 5 more links, https://dx.doi.org/10.5517/ccdc.csd.cc1m5nk0, https://dx.doi.org/10.5517/ccdc.csd.cc1m5nl1, https://dx.doi.org/10.5517/ccdc.csd.cc1m5nm2, https://dx.doi.org/10.5517/ccdc.csd.cc1m5nn3, https://dx.doi.org/10.5517/ccdc.csd.cc1m5np4 (show fewer)
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@article{99fff0eb48c24d3581ace81bc279be35,

title = "Application of four-membered ring chalcogenation reagents to the synthesis of new phosphorus-chalcogen heterocycles",

abstract = "The reaction of four-membered ring chalcogenation reagents such as Lawesson{\textquoteright}s reagent, 2,4-diferrocenyl-1,3,2,4-diathiadiphosphetane 2,4-disulfide (the ferrocene analogy of Lawesson{\textquoteright}s reagent) and Woollins{\textquoteright} reagent with alkyl- or aryl-dithiols in refluxing toluene gave a series of five- to seven-membered organo-phosphorus-chalcogen heterocycles in 24\% to 87\% yields. Five representative X-ray structures confirm the formation of these five- to seven-membered heterocycles. ",

keywords = "Lawesson{\textquoteright}s reagent, Woollins{\textquoteright} reagent, X-ray structure, Phosphorus‐chalcogen heterocycles, Chalcogenation, Dithiols",

author = "Guoxiong Hua and Cordes, \{David Bradford\} and Slawin, \{Alexandra Martha Zoya\} and Woollins, \{J Derek\}",

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

year = "2016",

month = aug,

day = "29",

doi = "10.3998/ark.5550190.p009.807",

language = "English",

volume = "2017",

pages = "9--20",

journal = "ARKIVOC",

issn = "1551-7004",

publisher = "Arkat",

number = "2",

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TY - JOUR

T1 - Application of four-membered ring chalcogenation reagents to the synthesis of new phosphorus-chalcogen heterocycles

AU - Hua, Guoxiong

AU - Cordes, David Bradford

AU - Slawin, Alexandra Martha Zoya

AU - Woollins, J Derek

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

PY - 2016/8/29

Y1 - 2016/8/29

N2 - The reaction of four-membered ring chalcogenation reagents such as Lawesson’s reagent, 2,4-diferrocenyl-1,3,2,4-diathiadiphosphetane 2,4-disulfide (the ferrocene analogy of Lawesson’s reagent) and Woollins’ reagent with alkyl- or aryl-dithiols in refluxing toluene gave a series of five- to seven-membered organo-phosphorus-chalcogen heterocycles in 24% to 87% yields. Five representative X-ray structures confirm the formation of these five- to seven-membered heterocycles.

AB - The reaction of four-membered ring chalcogenation reagents such as Lawesson’s reagent, 2,4-diferrocenyl-1,3,2,4-diathiadiphosphetane 2,4-disulfide (the ferrocene analogy of Lawesson’s reagent) and Woollins’ reagent with alkyl- or aryl-dithiols in refluxing toluene gave a series of five- to seven-membered organo-phosphorus-chalcogen heterocycles in 24% to 87% yields. Five representative X-ray structures confirm the formation of these five- to seven-membered heterocycles.

KW - Lawesson’s reagent

KW - Woollins’ reagent

KW - X-ray structure

KW - Phosphorus‐chalcogen heterocycles

KW - Chalcogenation

KW - Dithiols

U2 - 10.3998/ark.5550190.p009.807

DO - 10.3998/ark.5550190.p009.807

M3 - Article

SN - 1551-7004

VL - 2017

SP - 9

EP - 20

JO - ARKIVOC

JF - ARKIVOC

IS - 2

ER -

Application of four-membered ring chalcogenation reagents to the synthesis of new phosphorus-chalcogen heterocycles

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Application of four-membered ring chalcogenation reagents to the synthesis of new phosphorus-chalcogen heterocycles (dataset)

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