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2,2,2-Trichloro-4-methoxy-1,3,2-benzodioxaphosphole in the reactions with terminal acetylenes

Andrey Vladimirovich Nemtarev 1, 2
Andrey Vladimirovich Nemtarev
, 
Igor Olegovich Nasibullin 2
Igor Olegovich Nasibullin
, 
Robert Rustemovich Fayzullin 1
Robert Rustemovich Fayzullin
,  , 
Vladimir Fedorovich Mironov 1, 2
Vladimir Fedorovich Mironov
10.1016/j.mencom.2020.01.011
Published 2019-12-30
Communication , Volume 30, Issue 1, 34-37
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Nemtarev A. V. et al. 2,2,2-Trichloro-4-methoxy-1,3,2-benzodioxaphosphole in the reactions with terminal acetylenes // Mendeleev Communications. 2019. Vol. 30. No. 1. pp. 34-37.
GOST all authors (up to 50) Copy
Nemtarev A. V., Nasibullin I. O., Fayzullin R. R., Grigor’eva L. R., Mironov V. F. 2,2,2-Trichloro-4-methoxy-1,3,2-benzodioxaphosphole in the reactions with terminal acetylenes // Mendeleev Communications. 2019. Vol. 30. No. 1. pp. 34-37.
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TY - JOUR
DO - 10.1016/j.mencom.2020.01.011
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.01.011
TI - 2,2,2-Trichloro-4-methoxy-1,3,2-benzodioxaphosphole in the reactions with terminal acetylenes
T2 - Mendeleev Communications
AU - Nemtarev, Andrey Vladimirovich
AU - Nasibullin, Igor Olegovich
AU - Fayzullin, Robert Rustemovich
AU - Grigor’eva, Leysan Radikovna
AU - Mironov, Vladimir Fedorovich
PY - 2019
DA - 2019/12/30
PB - Mendeleev Communications
SP - 34-37
IS - 1
VL - 30
ER -
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@article{2019_Nemtarev,
author = {Andrey Vladimirovich Nemtarev and Igor Olegovich Nasibullin and Robert Rustemovich Fayzullin and Leysan Radikovna Grigor’eva and Vladimir Fedorovich Mironov},
title = {2,2,2-Trichloro-4-methoxy-1,3,2-benzodioxaphosphole in the reactions with terminal acetylenes},
journal = {Mendeleev Communications},
year = {2019},
volume = {30},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.01.011},
number = {1},
pages = {34--37},
doi = {10.1016/j.mencom.2020.01.011}
}
MLA
Cite this
MLA Copy
Nemtarev, Andrey Vladimirovich, et al. “2,2,2-Trichloro-4-methoxy-1,3,2-benzodioxaphosphole in the reactions with terminal acetylenes.” Mendeleev Communications, vol. 30, no. 1, Dec. 2019, pp. 34-37. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.01.011.

Keywords

arylacetylenes
cascade reactions
dioxaphospholes
ethenylphosphonic acids
oxaphosphinines
phosphoranes

Abstract

2,2,2-Trichloro-4-methoxy-1,3,2-benzodioxaphosphole reacts with arylacetylenes or 3-chloropropyne to give 2,7-dichloro-5-methoxy-4-aryl(haloalkyl)-1,2-benzoxaphosphinine 2-oxides. Hydrolysis of the latter leads to the opening of the oxaphosphinine ring and formation of (E)-2-(4-chloro-2- methoxy-6 hydroxyphenyl)ethenylphosphonic acid.

References

1.
10.1016/j.mencom.2020.01.011_sbref0005a
The Chemistry of Phenols, 2003
3.
Photostabilization of poly (p-phenylene sulfide)
Das P.K., DesLauriers P.J., Fahey D.R., Wood F.K., Cornforth F.J.
Polymer Degradation and Stability, 1995
4.
10.1016/j.mencom.2020.01.011_sbref0005d
Zweifel
Plastics Additives Handbook, 2009
7.
Microwave synthesis of secondary phosphines and phosphine oxides from red phosphorus and allyl(methoxy)benzenes in KOH-DMSO
Kuimov V.A., Malysheva S.F., Artem’ev A.V., Kenzhetaeva S.O., Belogorlova N.A., Komarova T.N., Gusarova N.K., Trofimov B.A.
Russian Journal of Organic Chemistry, 2014
8.
10.1016/j.mencom.2020.01.011_sbref0010a
Gardziella
Phenolic Resins: Chemistry, Applications, Standardization, Safety and Ecology, 2000
9.
10.1016/j.mencom.2020.01.011_sbref0010b
Phenolic Resins: A Century of Progress, 2010
10.
10.1016/j.mencom.2020.01.011_sbref0010c
Knop
Chemistry and Application of Phenolic Resins, 1979
11.
Phenolic resins—100years of progress and their future
Hirano K., Asami M.
Reactive and Functional Polymers, 2013
12.
10.1016/j.mencom.2020.01.011_bib0015
Phenolic Compounds in Food and Their Effects on Health, I ACS Symposium Series, 1992
13.
10.1016/j.mencom.2020.01.011_bib0020
Phenolic Compounds – Natural Sources, Importance and Applications, 2017
14.
10.1016/j.mencom.2020.01.011_sbref0025a
Corbridge
Phosphorus: Chemistry, Biochemistry and Technology, 2013
15.
10.1016/j.mencom.2020.01.011_sbref0025b
Phosphorus-Carbon Heterocyclic Chemistry: The Rise of a New Domain, 2001
16.
10.1016/j.mencom.2020.01.011_sbref0025c
Mann
Heterocyclic Derivatives of Phosphorus, Arsenic, Antimony and Bismuth, 1970
18.
10.1016/j.mencom.2020.01.011_sbref0025e
1,4-Cycloaddition Reaction: The Diels–Alder Reaction in Heterocyclic Syntheses, 1967
22.
Synthesis of (PIII, PIII)-, (PIII, PV)-, (PIII, PIV)-, (PIV, PV)-, and (PV, PV)-Diphosphorus-Containing Compounds Based on 1,2,3- and 1,2,4-Trihydroxybenzenes
Nemtarev A.V., Nasibullin I.O., Mironov V.F., Cherkasov V.K.
Phosphorus, Sulfur and Silicon and the Related Elements, 2015
24.
Reaction of arylenedioxytrihalophosphoranes with acetylenes 11. Electronic effect of the substituent in arylacetylene on the reaction rate
Nemtarev A.V., Mironov V.F., Aniskin A.S., Baranov D.S., Mironova E.V., Krivolapov D.B., Musin R.Z., Vasilevskii S.F., Druzhkov N.O., Cherkasov V.K.
Russian Chemical Bulletin, 2013
26.
Regioselectivity of the reaction of 4,6-di-tert-butyl-2,2,2-trichloro-1,3, 2λ5-benzodioxaphosphole with hex-1-yne. ipso substitution of tert-butyl group
Nemtarev A.V., Varaksina E.N., Mironov V.F., Musin R.Z., Konovalov A.I.
Russian Journal of Organic Chemistry, 2007
27.
Reaction of arylenedioxytrihalophosphoranes with acetylenes 12. Alkylacetylenes in the reaction with 2,2,2-trihalobenzo-1,3,2-dioxaphospholes
Nemtarev A.V., Mironov V.F., Varaksina E.N., Gubaidullin A.T., Krivolapov D.B., Musin R.Z., Litvinov I.A.
Russian Chemical Bulletin, 2014
28.
Nemtarev A.V., Varaksina E.N., Mironov V.F., Musin R.Z., Konovalov A.I.
Mendeleev Communications, 2006
29.
Spirophosphoranylation d'α-aminoacides—I
Garrigues B., Munoz A., Koenig M., Sanchez M., Wolf R.
Tetrahedron, 1977
30.
Hexacoordination du phosphore par complexation intramoleculaire
Cong C.B., Gence G., Garrigues B., Koenig M., Munoz A.
Tetrahedron, 1979
31.
10.1016/j.mencom.2020.01.011_bib0055
Kuhl
Phosphorus-31 NMR Spectroscopy, 2008
32.
SHELXT– Integrated space-group and crystal-structure determination
Sheldrick G.M.
Acta Crystallographica Section A: Foundations and Advances, 2015
33.
Crystal structure refinement withSHELXL
Sheldrick G.M.
Acta crystallographica. Section C, Structural chemistry, 2015