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.