New synthesis of trimethylsilyl esters of phosphorus(III) acids

被引：3

作者：

Morgalyuk, Vasily ^{[1
]}

Strelkova, Tatyana ^{[1
]}

Brel, Valery ^{[1
]}

机构：

[1] Russian Acad Sci, Nesmeyanov Inst Organoelement Cpds, Ul Vavilova 28, Moscow 119991, Russia

来源：

MONATSHEFTE FUR CHEMIE | 2019年 / 150卷 / 11期

关键词：

Phosphorus(III) trimethylsilylether; Phosphorus compounds; Reaction mechanisms; Retro reactions; REARRANGEMENT; REACTIVITY;

D O I：

10.1007/s00706-019-02511-6

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel synthetically important reaction has been developed for the quick, convenient, and high-yield preparation of trimethylsilyl esters of phosphorus(III) acids, synthetically valuable Michaelis-Arbuzov reaction precursors. Commercially and synthetically available initial compounds used are derivatives of propan-2-ol phosphorylated in the second position capable of long-term storage and available silylating reagents: hexamethyldisilazane, bis(trimethylsilyl)acetamide, and diethyl(trimethylsilyl)amine. Also, a stepwise reaction scheme of the starting compounds with silylating reagents has been proposed. [GRAPHICS]

引用

页码：1993 / 1997

页数：5

共 50 条

[21] Synthesis and thermal stability of S-trimethylsilyl esters of tetracoordinated phosphorus amidothioacids
Nizamov, Il'yas S.
Bolshakova, Olga V.
Al'metkina, Lyubov A.
Nizamov, Il'nar D.
Sergeenko, Gulnur G.
Frolova, Liliya V.
Krivolapov, Dmitry B.
Batyeva, Elvira S.
Litvinov, Igor A.
HETEROATOM CHEMISTRY, 2006, 17 (07) : 670 - 675
[22] SYNTHESIS OF ESTERS OF ISOPROPYLIDENE GLYCERIN AND SOME ACIDS OF PHOSPHORUS
MIZRAKH, LI
POLONSKAYA, LY
VORONTSOV, ED
ZHURNAL OBSHCHEI KHIMII, 1983, 53 (02): : 426 - 430
[23] A NEW METHOD FOR SYNTHESIS OF PHOSPHINIC AND THIOPHOSPHINIC ACIDS .35. ADDITION OF PHOSPHORUS PENTACHLORIDE TO DIENE HYDROCARBONS AND OF ACIDIC ESTERS OF PHOSPHORUS ACIDS TO BUTADIENE PHOSPHINIC ESTERS
PUDOVIK, AN
KONOVALOVA, IV
ZHURNAL OBSHCHEI KHIMII, 1961, 31 (05): : 1693 - &
[24] INTRAMOLECULAR EXCHANGE OF TRIMETHYLSILYL GROUP IN TRIMETHYLSILYL ESTERS OF NITRONIC ACIDS
IOFFE, SL
SHITKIN, VM
KHASAPOV, BN
KASHUTIN.MV
TARTAKOV.VA
MYAGI, MY
LIPPMAA, ET
IZVESTIYA AKADEMII NAUK SSSR-SERIYA KHIMICHESKAYA, 1973, (09): : 2146 - 2148
[25] SYNTHESIS OF AZIRIDIDES OF QUINQUEVALENT PHOSPHORUS ACIDS FROM ACID ESTERS AND AMIDES OF TERVALENT PHOSPHORUS ACIDS
NIFANTEV, EE
ZAVALISH.AI
JOURNAL OF GENERAL CHEMISTRY USSR, 1967, 37 (08): : 1766 - &
[26] ADDITION-REACTIONS OF ESTERS OF PHOSPHORUS(III) ACIDS WITH UNSATURATED SYSTEMS
PUDOVIK, AN
KONOVALOVA, IV
SYNTHESIS-STUTTGART, 1979, (02): : 81 - 96
[27] CATALYTIC METHODS OF SYNTHESIS OF POLYFLUOROALKYL ESTERS OF PHOSPHORUS-ACIDS
KABACHNIK, MI
ZAKHAROV, LS
GORYUNOV, EI
KUDRYAVTSEV, IY
MOLCHANOVA, GN
KURYKIN, MA
PETROVSKII, PV
SHCHERBINA, TM
LARETINA, AP
ZHURNAL OBSHCHEI KHIMII, 1994, 64 (06): : 902 - 912
[28] SYNTHESIS OF CHLORINE-CONTAINING CYCLIC ESTERS OF PHOSPHORUS ACIDS
SHAPOVAL.AN
SHNER, SM
JOURNAL OF GENERAL CHEMISTRY USSR, 1968, 38 (02): : 318 - &
[29] Catalytic synthesis of alpha-trichloromethylbenzyl esters of phosphorus acids
Goryunov, EI
Molchanova, GN
Petrovskii, PV
Shcherbina, TM
Laretina, AP
Zakharov, LS
Kabachnik, MI
RUSSIAN CHEMICAL BULLETIN, 1995, 44 (11) : 2202 - 2202
[30] TRIMETHYLSILYL ESTERS OF PHOSPHORUS ACIDS .1. PREPARATION AND PROPERTIES OF ESTERS OF (DIFLUOROMETHYL)PHOSPHINIC AND BIS(TRIFLUOROMETHYL)PHOSPHINIC (TRIFLUOROMETHYL)THIOPHOSPHONIC, AND (TRIFLUOROMETHYL)DITHIOPHOSPHINIC ACIDS
CAVELL, RG
TOMLINSO.AJ
LEARY, RD
INORGANIC CHEMISTRY, 1972, 11 (11) : 2573 - &

← 1 2 3 4 5 →