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One-pot three-component condensation synthesis and structural features of organophosphorus-sulfur macrocycles
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dc.contributor.author | Hua, Guoxiong | |
dc.contributor.author | Du, Junyi | |
dc.contributor.author | Cordes, David Bradford | |
dc.contributor.author | Slawin, Alexandra Martha Zoya | |
dc.contributor.author | Woollins, John Derek | |
dc.date.accessioned | 2017-05-02T23:33:45Z | |
dc.date.available | 2017-05-02T23:33:45Z | |
dc.date.issued | 2016-05-20 | |
dc.identifier | 242417009 | |
dc.identifier | e52ccca7-00d1-40fd-8327-31807fc8a554 | |
dc.identifier | 84971265240 | |
dc.identifier | 000376476400026 | |
dc.identifier.citation | Hua , G , Du , J , Cordes , D B , Slawin , A M Z & Woollins , J D 2016 , ' One-pot three-component condensation synthesis and structural features of organophosphorus-sulfur macrocycles ' , The Journal of Organic Chemistry , vol. 81 , no. 10 , pp. 4210-4225 . https://doi.org/10.1021/acs.joc.6b00573 | en |
dc.identifier.issn | 0022-3263 | |
dc.identifier.other | ORCID: /0000-0002-5366-9168/work/28023979 | |
dc.identifier.other | ORCID: /0000-0002-9527-6418/work/56861608 | |
dc.identifier.other | ORCID: /0000-0002-1498-9652/work/31779162 | |
dc.identifier.uri | https://hdl.handle.net/10023/10695 | |
dc.description | We are grateful to the University of St. Andrews for financial support and the EPSRC National Mass Spectrometry Service Centre (Swansea) for mass spectral measurements. | en |
dc.description.abstract | A new preparative route was developed to synthesize new phosphorus–sulfur [SP(═S)S moiety]-containing macrocycles via a one-pot and three-component domino reaction of four-membered ring thionation reagents such as 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (LR, Lawesson’s reagent) and 2,4-diferrocenyl-1,3,2,4-diathiadiphosphetane 2,4-disulfide (FcLR, a ferrocene analogue of Lawesson’s reagent) and alkyldithiols(aryldithols) and dihaloalkanes in the presence of sodium hydride. Therefore, a series of 12- to 18-membered macrocycles incorporating two phosphorus and six sulfur atoms were synthesized. The synthesis features a novel application of the multicomponent reaction, providing an efficient route to the preparation of the new phosphorus–sulfur-containing macrocycles. Seven representative X-ray structures confirm the formation of these macrocycles and show the presence of a number of the intramolecular C–H···S hydrogen bonding, intermolecular C–H···S, C–H···Cl, and Cl···Cl short contacts and π-stacking interactions in their 3D network structures. | |
dc.format.extent | 16 | |
dc.format.extent | 13265465 | |
dc.format.extent | 4963112 | |
dc.language.iso | eng | |
dc.relation.ispartof | The Journal of Organic Chemistry | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject.lcc | QD | en |
dc.title | One-pot three-component condensation synthesis and structural features of organophosphorus-sulfur macrocycles | en |
dc.type | Journal article | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.contributor.institution | University of St Andrews. Office of the Principal | en |
dc.identifier.doi | 10.1021/acs.joc.6b00573 | |
dc.description.status | Peer reviewed | en |
dc.date.embargoedUntil | 2017-05-02 |
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