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One-pot three-component condensation synthesis and structural features of organophosphorus-sulfur macrocycles

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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.
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Original languageEnglish
Pages (from-to)4210-4225
Number of pages16
JournalJournal of Organic Chemistry
Volume81
Issue number10
Early online date2 May 2016
DOIs
Publication statusPublished - 20 May 2016

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