223436-62-2Relevant academic research and scientific papers
Synthesis and some transformations of 1,2-heterophosphacyclanes
Mastryukova, Tatyana A.,Aladzheva, Inga M.,Lobanov, Dmitrii I.,Bykhovskaya, Olga V.,Petrovskii, Pavel V.,Lyssenko, Konstantin A.,Kabachnik, Martin I.
, p. 569 - 572 (2007/10/03)
The general pathway to 1,2-monoheterophosphacyclanes via intramolecular S-and N-alkylation of ω-halogenoalkylsubstituted thiophosphoryl and iminophosphoryl compounds has been developed. Intramolecular alkylation of 3-and 4-halogenoalkyldiphenylphosphine sulfides results in 1,2λ4-thiaphospholanium and thiaphosphorinanium halogenides. In solution of these compounds the rare ring-chain halogenotropic tautomerism has been observed and investigated in detail. Intramolecular Pishchimuka rearrangement of the esters of ω-halogenoalkylsubstituted thiophosphorus acids was found to be a synthetic route to 2-oxo-1,2ω5-thiaphospholanes and thiaphosphorinanes.
1,2-Thiaphosphacyclanes. Synthesis, Tautomerism, and Reactivity
Aladzheva,Bykhovskaya,Lobanov,Petrovskii,Lysenko,Antipin,Mastryukova,Kabachnik
, p. 1356 - 1367 (2007/10/03)
A method of synthesis of 1,2-thiaphophacyclanes is proposed, relying on intramolecular alkylation of ω-haloalkyl-substituted organophosphorus compounds with a phosphinothioyl group. Alkylation of (3-haloalkyl)- and (4-haloalkyl)diphenylphosphine sulfides leads to 1,2λ4-thiaphospholanium and 1,2λ4-thiaphosphorinanium salts, 1,2λ4-Thiaphosphacyclanium salts we found to undergo ring-chain tautomerism. Individual tautomeric bromides were isolated, and their mutual transformations in solutions were studied, as well as thermodynamic and kinetic parameters of the tautomeric equilibrium were estimated. Hydrolysis of 1,2λ4-thiaphospholanium and 1,2λ4-thiaphosphorinanium salts and their anion exchange reactions were studied. Alkylation of 3- and 4-haloalkyl-substiluted phosphorus thioacid esters is accompanied by intramolecular Pistschimuka rearrangement yielding 1,2λ5-thiaphospholane 2-oxides and 1,2λ5-thiaphosphorinane 2-oxides.
