Simultaneous Formation of Cage and Spirane Pentaalkoxyphosphoranes in Reaction of 5,5-Dimethyl-2-(2-oxo-1,2-diphenylethoxy)-1,3,2-dioxaphosphorinane with Hexafluoroacetone

被引:2
|
作者
Mironov, V. F. [1 ,2 ]
Dimukhametov, M. N. [1 ]
Blinova, Ya. S. [2 ]
Karataeva, F. Kh. [2 ]
机构
[1] Russian Acad Sci, Kazan Sci Ctr, Fed Res Ctr, Arbuzov Inst Organ & Phys Chem, Kazan 420088, Russia
[2] Kazan Volga Reg Fed Univ, Kazan 420008, Russia
基金
俄罗斯基础研究基金会;
关键词
dioxaphosphorinane; hexafluoroacetone; cage phosphorane; PCO; POC-rearrangement; spirophosphorane; hydrolysis; phosphate; NUCLEAR-MAGNETIC-RESONANCE; P-C; PHOSPHATE REARRANGEMENT; PHOSPHORUS-CARBON; CRYSTAL-STRUCTURE; HYDROLYSIS; SPIROPHOSPHORANES; FLUOROPHOSPHONIUM; ACTIVATION; NMR;
D O I
10.1134/S1070363220110109
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The reaction of hexafluoroacetone with 5,5-dimethyl-2-(2-oxo-1,2-diphenylethoxy)-1,3,2-dioxaphosphorinane occurs in two simultaneous directions: through the formation of cage phosphorane and spirophosphorane-1,1-(2,2-dimethylpropylenedioxy)-4,5-diphenyl-3,3-bis(trifluoromethyl)-2,6,7-trioxa-1-phosphabicyclo[2.2.1(1.4)]heptane and 2-(2,2-dimethylpropylenedioxy)-2-hexafluoroisopropoxy-4,5-diphenyl-1,3,2-dioxaphospholene, respectively. The latter was obtained by authentic synthesis from 2-hexafluoroisopropoxy-5,5-dimethyl-1,3,2-dioxaphosphorinane and benzil. The mild hydrolysis of the compounds obtained leads to the formation of cyclic phosphates. The structure of the obtained compounds was determined by the NMR and mass spectrometry methods.
引用
收藏
页码:2080 / 2092
页数:13
相关论文
共 50 条
  • [21] Synthesis, crystal structure and hydrolysis of novel isomeric cage (P-C/P-O)-phosphoranes on the basis of 4,4,5,5-tetramethyl-2-(2-oxo-1,2-diphenylethoxy)-1,3,2-dioxaphospholane and hexafluoroacetone
    Khasiyatullina, Nadezhda R.
    Mironov, Vladimir F.
    Krivolapov, Dmitry B.
    Mironova, Ekaterina V.
    Gnezdilov, Oleg I.
    RSC ADVANCES, 2016, 6 (89): : 85745 - 85755
  • [22] MOLECULAR-STRUCTURE OF 2-PHENOXY-2-THIONO-5,5-DIMETHYL 1,3,2-DIOXAPHOSPHORINANE
    GRAND, A
    ROBERT, JB
    ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1975, 31 (OCT15): : 2502 - 2503
  • [23] Carbanionic displacement reactions at phosphorus: Synthesis and reactivity of 5,5-dimethyl-2-oxo-2-(1,3-dithian-2-yl)-1,3,2-dioxaphosphorinane
    Iorga, B
    Mouries, V
    Savignac, P
    BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, 1997, 134 (10-11): : 891 - 895
  • [24] 5,5-Dimethyl-2-[6-methyl-2-(methylsulfanyl)pyrimidin-4-yloxy]-1,3,2-dioxaphosphorinane-2-thione
    Pop, M
    Borodi, G
    Goubitz, K
    Peschar, R
    Fraanje, J
    Fenesan, I
    Schenk, H
    ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2002, 58 : o280 - o281
  • [26] STUDIES OF ORGANOPHOSPHORUS DERIVATIVES PART .1. NUCLEAR MAGNETIC-RESONANCE STUDIES OF 2-OXO-1,3,2-DIOXAPHOSPHORINANE SYSTEM
    HALL, LD
    MALCOLM, RB
    CANADIAN JOURNAL OF CHEMISTRY, 1972, 50 (13): : 2092 - &
  • [27] VIBRATIONAL-SPECTRA AND CONFORMATIONS OF 2-THIO-2-METHYL-1,3,2-DIOXAPHOSPHORINANE AND ITS 5,5-DIMETHYL DERIVATIVE
    SHAGIDULLIN, RR
    SHAKIROV, IK
    MUSYAKAEVA, RK
    NURETDINOV, IA
    BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1981, 30 (08): : 1557 - 1559
  • [28] QUANTITATIVE REGULARITIES OF CATALYSIS OF 2-ETHYLPHENYLAMINO-5,5-DIMETHYL-1,3,2-DIOXAPHOSPHORINANE METHANOLYSIS BY 1,2,4-TRIAZOLE
    NIFANTEV, EE
    GRACHEV, MK
    BURMISTROV, SY
    SHCHEDROVA, NM
    VASYANINA, LK
    DOKLADY AKADEMII NAUK, 1994, 339 (05) : 631 - 634
  • [29] STRUCTURE OF 5,5-DIMETHYL-2-PHENYLAMINO-1,3,2-DIOXAPHOSPHORINANE 2-SELENIDE, C11H16NO2PSE
    BARTCZAK, TJ
    GALDECKI, Z
    TRZEZWINSKA, HB
    WOLF, W
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1983, 39 (JUN) : 731 - 732
  • [30] Syntheses and spectral characterization of 2-aryloxy-5,5′-bis(bromomethyl)-1,3,2-dioxaphosphorinane 2-oxides
    Babu, MFS
    Anasuyamma, U
    Venugopal, M
    Raju, CN
    Reddy, CS
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2005, 44 (06): : 1248 - 1251