Reaction of 5-oxo-2-phenyl-4,4-bis(trifluoromethyl)-4,5-dihydro-1,3,2- benzodioxaphosphepine with chloral. the synthesis and spatial structure of 5-carbaphosphatrane containing a four-membered ring
V F Mironov
1, 2
,
Yu Yu Borisova
2
,
L. M. Burnaeva
2
,
A.T. Gubaidullin
1
,
A B Dobrynin
1
,
I A Litvinov
1
,
R Z Musin
1
,
I. V. Konovalova
2
Publication type: Journal Article
Publication date: 2010-04-01
scimago Q3
SJR: 0.305
CiteScore: 2.8
Impact factor: —
ISSN: 10665285, 15739171
General Chemistry
Abstract
Phosphorylation of 2-hydroxyphenyl 2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl ketone with dichloro(phenyl)phosphine gave 5-oxo-2-phenyl-4,4-bis(trifluoromethyl)-4,5-di-hydro-1,3,2-benzodioxaphosphepine. Heating of the latter initiated an intramolecular interaction of the P atom with the carbonyl group. Hydrolysis of the intermediate product yielded 3-hydroxy-2-oxo-2-phenyl-3-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-2,3-di-hydro-1,2λ5-benzo[d]oxaphosphole. The reaction was highly stereoselective (PRCS/PSCR). The reaction of the starting phosphepine with chloral proceeded highly stereoselectively (PRCSCS/PSCRCR) to give a 5-carbaphosphatrane derivative containing a four-membered ring, namely, 1-phenyl-3-trichloromethyl-10,10-bis(trifluoromethyl)-6,7-benzo-2,4,8,9-tetraoxa-1λ5-phosphatricyclo[3.3.2.01,5]decene. The trigonal bipyramid of the 5-carbaphosphatrane derivative is made up of the equatorial O atoms and the apical C atoms.
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Mironov V. F. et al. Reaction of 5-oxo-2-phenyl-4,4-bis(trifluoromethyl)-4,5-dihydro-1,3,2- benzodioxaphosphepine with chloral. the synthesis and spatial structure of 5-carbaphosphatrane containing a four-membered ring // Russian Chemical Bulletin. 2010. Vol. 59. No. 4. pp. 820-827.
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Mironov V. F., Borisova Yu. Yu., Burnaeva L. M., Gubaidullin A., Dobrynin A. B., Litvinov I. A., Musin R. Z., Konovalova I. V. Reaction of 5-oxo-2-phenyl-4,4-bis(trifluoromethyl)-4,5-dihydro-1,3,2- benzodioxaphosphepine with chloral. the synthesis and spatial structure of 5-carbaphosphatrane containing a four-membered ring // Russian Chemical Bulletin. 2010. Vol. 59. No. 4. pp. 820-827.
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TY - JOUR
DO - 10.1007/s11172-010-0167-3
UR - https://doi.org/10.1007/s11172-010-0167-3
TI - Reaction of 5-oxo-2-phenyl-4,4-bis(trifluoromethyl)-4,5-dihydro-1,3,2- benzodioxaphosphepine with chloral. the synthesis and spatial structure of 5-carbaphosphatrane containing a four-membered ring
T2 - Russian Chemical Bulletin
AU - Mironov, V F
AU - Borisova, Yu Yu
AU - Burnaeva, L. M.
AU - Gubaidullin, A.T.
AU - Dobrynin, A B
AU - Litvinov, I A
AU - Musin, R Z
AU - Konovalova, I. V.
PY - 2010
DA - 2010/04/01
PB - Springer Nature
SP - 820-827
IS - 4
VL - 59
SN - 1066-5285
SN - 1573-9171
ER -
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@article{2010_Mironov,
author = {V F Mironov and Yu Yu Borisova and L. M. Burnaeva and A.T. Gubaidullin and A B Dobrynin and I A Litvinov and R Z Musin and I. V. Konovalova},
title = {Reaction of 5-oxo-2-phenyl-4,4-bis(trifluoromethyl)-4,5-dihydro-1,3,2- benzodioxaphosphepine with chloral. the synthesis and spatial structure of 5-carbaphosphatrane containing a four-membered ring},
journal = {Russian Chemical Bulletin},
year = {2010},
volume = {59},
publisher = {Springer Nature},
month = {apr},
url = {https://doi.org/10.1007/s11172-010-0167-3},
number = {4},
pages = {820--827},
doi = {10.1007/s11172-010-0167-3}
}
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MLA
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Mironov, V. F., et al. “Reaction of 5-oxo-2-phenyl-4,4-bis(trifluoromethyl)-4,5-dihydro-1,3,2- benzodioxaphosphepine with chloral. the synthesis and spatial structure of 5-carbaphosphatrane containing a four-membered ring.” Russian Chemical Bulletin, vol. 59, no. 4, Apr. 2010, pp. 820-827. https://doi.org/10.1007/s11172-010-0167-3.