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.
Original language | English |
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Pages (from-to) | 4210-4225 |
Number of pages | 16 |
Journal | The Journal of Organic Chemistry |
Volume | 81 |
Issue number | 10 |
Early online date | 2 May 2016 |
DOIs | |
Publication status | Published - 20 May 2016 |
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One-pot three-component condensation synthesis and structural features of organophosphorus-sulfur macrocycles (dataset)
Hua, G. (Creator), Du, J. (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.cc1l9f2d and 6 more links, https://dx.doi.org/10.5517/ccdc.csd.cc1l9f3f, https://dx.doi.org/10.5517/ccdc.csd.cc1l9f4g, https://dx.doi.org/10.5517/ccdc.csd.cc1l9f5h, https://dx.doi.org/10.5517/ccdc.csd.cc1l9f6j, https://dx.doi.org/10.5517/ccdc.csd.cc1l9f7k, https://dx.doi.org/10.5517/ccdc.csd.cc1l9f8l (show fewer)
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