- Synthesis and thermal stability of silicon-containing esters of phosphorus acids 5.* the relative migration ability of substituents at the silicon atom in the thermal rearrangement of trialkylsilylmethyl diphenyl phosphates
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A number of trialkylsilylmethyl diphenyl phosphates MeRR'SiCH2OP(O)(OPh)2 (Ia-e: R = Et (a), Pr (b), CF3CH2CH2 (c, e), Me3SiCH2 (d); R' = Me (a-d), Et (e)) were synthesized and their thermal rearrangement, of the 1,2-shift type, was studied. The rearrangement consists of the migration of an alkyl group from Si atom to the methylene carbon atom and gives the corresponding silyl esters. The rate of the rearrangement was found to increase in the order 1d 3CH2CH2 3SiCH2, which differs substantially from the order in which the rate of the rearrangement of phosphates 1a-d changes. The electro-negativity of the migrating group affects noticeably the relative ability to migrate.
- Zakharov,Molchanova,Shcherbina,Petrovskii,Kabachnik
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p. 1718 - 1724
(2007/10/03)
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