N-alkylation of amidothiophosphoryl compounds under phase-transfer catalysis conditions. Synthesis and properties of 1,3,2-thiazaphosphacyclanes |
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Authors: | O. I. Artyushin E. V. Sharova P. V. Petrovskii I. L. Odinets |
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Affiliation: | (1) N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Novosibirsk, Russia; |
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Abstract: | N (ω-Haloalkyl)amidothiophosphates, N (ω-Haloalkyl)amidothiophosphonates, and N- (ω-Haloalkyl)amidothiophosphinates (Hal = Cl or Br) were obtained in high yields by alkylation of phosphorus(V) acid thioamides with 6h,ω-dihaloalkanes under phase-transfer catalysis (PTC) conditions or through the use of NaH as a base. Thermal rearrangement of N (3-iodopropyl)-or N (4-iodobutyl)amidothiophosphate and N (3-iodopropyl)-or N (4-iodo-butyl)amidothiophosphonate obtained in situ by the Finkelstein reaction provides a convenient route to 2-oxo-1,3,2-thiazaphosphinanes and 2-oxo-1,3,2-thiazaphosphepanes. Reactions of N (ω-Haloalkyl)amidothiophosphinates with NaClO4 in MeCN afforded the first example of stable 1,3,2-thiazaphosphacyclanium salts containing P—C bonds. |
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