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One-Pot Three-Component Condensation Synthesis and Structural Features of Organophosphorus–Sulfur Macrocycles

2016; American Chemical Society; Volume: 81; Issue: 10 Linguagem: Inglês

10.1021/acs.joc.6b00573

1520-6904

Guoxiong Hua, Junyi Du, David B. Cordes, Alexandra M. Z. Slawin, J. Derek Woollins,

Sulfur-Based Synthesis Techniques

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.