Tetrahedron 2018-02-25

Synthetic studies on a series of functionalized pyrylium salts, 4-chloro- and 4-bromophosphinines

Noriyoshi Nagahora, Hiroshi Tokumaru, Shinpei Ikaga, Takuya Hanada, Kosei Shioji, Kentaro Okuma

Index: 10.1016/j.tet.2018.02.053

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Abstract

A series of new pyrylium salts that bear sulfonate and phosphonate groups were obtained from the reactions between 2,6-diphenyl-4H-pyran-4-one, sulfonic anhydride, and chlorophosphates, and analyzed spectroscopically. Furthermore, treatment of 2,6-diphenyl-4H-pyran-4-one with phosphoryl chloride or bromide afforded the corresponding 4-chloro- and 4-bromopyrylium tetrafluoroborates in good yield. Subsequently, the synthesis of the corresponding 4-chloro- and 4-bromophosphinines was accomplished by treating the respective chloro- and bromopyrylium tetrafluoroborates with tris(trimethylsilyl)phosphine.

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