One-Pot Approach to Organo-Phosphorus-Chalcogen Macrocycles Incorporating Double OP(S)SCn or OP(Se)SeCn Scaffolds: A Synthetic and Structural Study.
The development of new methodology for the preparation of functional macrocycles with practical applications is an 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 macrocycles 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.
EastChem School of Chemistry, University of St. Andrews, St. Andrews, Fife, KY16 9ST, UK.
Guoxiong
G
Hua
EastChem School of Chemistry, University of St. Andrews, St. Andrews, Fife, KY16 9ST, UK.
Junyi
J
Du
EastChem School of Chemistry, University of St. Andrews, St. Andrews, Fife, KY16 9ST, UK.
Alexandra M Z
0000-0002-9527-6418
AM
Slawin
EastChem School of Chemistry, University of St. Andrews, St. Andrews, Fife, KY16 9ST, UK. jdw3@st-andrews.ac.uk.
J Derek
0000-0002-1498-9652
JD
Woollins
Lawesson's reagent; Woollins’ reagent; cyclization; macrocycles; structure elucidation