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The reaction of 4-(1,3,2-benzodioxaphosphol-2-yloxy)-3-tert-butylpent-4-en-2-one with hexafluoroacetone

Vladimir Fedorovich Mironov 1, 2
Vladimir Fedorovich Mironov
, 
Tamara Aleksandrovna Baronova 1, 2
Tamara Aleksandrovna Baronova
, 
Mudaris Nurgaleevich Dimukhametov 1
Mudaris Nurgaleevich Dimukhametov
, 
Robert Rustemovich Fayzullin 1
Robert Rustemovich Fayzullin
, 
Igor Anatol'evich Litvinov 1
Igor Anatol'evich Litvinov
10.1016/j.mencom.2019.09.009
Published 2019-09-04
Communication , Volume 29, Issue 5, 506-508
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Mironov V. F. et al. The reaction of 4-(1,3,2-benzodioxaphosphol-2-yloxy)-3-tert-butylpent-4-en-2-one with hexafluoroacetone // Mendeleev Communications. 2019. Vol. 29. No. 5. pp. 506-508.
GOST all authors (up to 50) Copy
Mironov V. F., Baronova T. A., Dimukhametov M. N., Fayzullin R. R., Litvinov I. A. The reaction of 4-(1,3,2-benzodioxaphosphol-2-yloxy)-3-tert-butylpent-4-en-2-one with hexafluoroacetone // Mendeleev Communications. 2019. Vol. 29. No. 5. pp. 506-508.
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TY - JOUR
DO - 10.1016/j.mencom.2019.09.009
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.09.009
TI - The reaction of 4-(1,3,2-benzodioxaphosphol-2-yloxy)-3-tert-butylpent-4-en-2-one with hexafluoroacetone
T2 - Mendeleev Communications
AU - Mironov, Vladimir Fedorovich
AU - Baronova, Tamara Aleksandrovna
AU - Dimukhametov, Mudaris Nurgaleevich
AU - Fayzullin, Robert Rustemovich
AU - Litvinov, Igor Anatol'evich
PY - 2019
DA - 2019/09/04
PB - Mendeleev Communications
SP - 506-508
IS - 5
VL - 29
ER -
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@article{2019_Mironov,
author = {Vladimir Fedorovich Mironov and Tamara Aleksandrovna Baronova and Mudaris Nurgaleevich Dimukhametov and Robert Rustemovich Fayzullin and Igor Anatol'evich Litvinov},
title = {The reaction of 4-(1,3,2-benzodioxaphosphol-2-yloxy)-3-tert-butylpent-4-en-2-one with hexafluoroacetone},
journal = {Mendeleev Communications},
year = {2019},
volume = {29},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.09.009},
number = {5},
pages = {506--508},
doi = {10.1016/j.mencom.2019.09.009}
}
MLA
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MLA Copy
Mironov, Vladimir Fedorovich, et al. “The reaction of 4-(1,3,2-benzodioxaphosphol-2-yloxy)-3-tert-butylpent-4-en-2-one with hexafluoroacetone.” Mendeleev Communications, vol. 29, no. 5, Sep. 2019, pp. 506-508. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2019.09.009.

Abstract

Catalytic (ZnCl2, Et3N) phosphorylation of tert-butylacetylacetone with 2-chloro-1,3,2-benzodioxaphosphole unexpectedly occurs with elimination of proton from the methyl group and leads to vinyloxyphosphole derivative, viz., 4-(1,3,2-benzodioxaphosphol-2-yloxy)-3-tert-butylpent-4-en-2-one. Its reaction with hexafluoroacetone gives a cage phosphorane as a result of subsequent chemoselective [4+2]- and [3+2]-cycloadditions with stereoselectivity above 95%.

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