One-pot approach to organo phosphorus-chalcogen macrocycles incorporating double OP(S)SCn or OP(Se)SeCn scaffolds : a synthetic and structural study
Abstract
The development of new methodology for the preparation of functional macrocycles with practical applications is a fundamental important research area in macromolecular science. In this study, we report a new one-pot route for the synthesis of a series of macro-heterocycles by incorporating two phosphorus atoms and two chalcogen atoms and two oxygen atoms (double OP(S)SCn or OP(Se)SeCn scaffolds). The three-component condensation reactions of 2,4-diferrocenyl-1,3,2,4-diathiadiphosphetane 2,4-disulfide ( FcLR , a ferrocene analogue of Lawesson’s reagent) or 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide ( LR , Lawesson’s reagent), or 2,4-diphenyl-1,3,2,4-diselenadiphosphetane 2,4-diselenide ( WR , Woollins’ reagent), disodium alkenyl-diols, and dihalogenated alkanes are performed giving rise to soluble and air or moisture-stable macrocycloes in good to excellent yields (up to 92%). This is the first systemically preparative and readily scalable example of one-pot ring opening/ring extending reaction of three-components to prepare phosphorus-chalcogen containing macrocycles. We also provide a systematic crystallographic study.
Citation
Hua , G , Du , J , Slawin , A M Z & Woollins , J D 2016 , ' One-pot approach to organo phosphorus-chalcogen macrocycles incorporating double OP(S)SC n or OP(Se)SeC n scaffolds : a synthetic and structural study ' , Chemistry - A European Journal , vol. 22 , no. 23 , pp. 7782-7791 . https://doi.org/10.1002/chem.201504832
Publication
Chemistry - A European Journal
Status
Peer reviewed
ISSN
0947-6539Type
Journal article
Rights
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This work is made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://dx.doi.org/10.1002/chem.201504832 © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This work is made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://dx.doi.org/10.1002/chem.201504832
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.Collections
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