Adducts of Mn and Re vinylidenes with P–OR nucleophiles: Hydrolysis rather than the intramolecular Michaelis–Arbuzov rearrangement
Kamil I Utegenov
1
,
Vasily V Krivykh
1
,
Oleg S. Chudin
2
,
Alexander F. Smol’yakov
3
,
Fedor Dolgushin
1
,
Oleg V. Semeikin
1
,
Nikolai A Shteltser
1
,
N. A. Ustynyuk
1
Publication type: Journal Article
Publication date: 2018-07-01
scimago Q3
wos Q2
SJR: 0.385
CiteScore: 4.1
Impact factor: 2.4
ISSN: 0022328X, 18728561
Materials Chemistry
Organic Chemistry
Biochemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
The reactions of vinylidene complexes Ср(CO)2Mn = C=C(H)Ph (Mn1) and Cp(CO)2Re = C=C(H)Ph (Re1) with P–OR nucleophiles P(OR)R'R (OR = R' = R = OMe, OEt, OPri, OPh; OR = OEt, R' = R = Ph; OR = R' = OEt, R = Ph) proceed as nucleophilic addition to the Cα vinylidene atom to initially afford zwitter-ionic complexes Z-Ср(CO)2M¯−C[+P(OR)R'R] = C(H)Ph which were identified by spectroscopic methods and, in some cases, their molecular structures were confirmed by X-ray diffraction. These adducts are extremely sensitive to water and hydrolyzed by water traces to afford the corresponding η2-phosphorylalkene complexes Cp(CO)2M{η2-E-HC[P(O)R'R] = C(H)Ph}. The isotopic label experiments with D2O and H218O showed the hydrolysis to proceed with the phosphorus–oxygen bond cleavage and binding of the water hydrogen to the carbon atom bearing the > P=O group.
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Utegenov K. I. et al. Adducts of Mn and Re vinylidenes with P–OR nucleophiles: Hydrolysis rather than the intramolecular Michaelis–Arbuzov rearrangement // Journal of Organometallic Chemistry. 2018. Vol. 867. pp. 113-124.
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Utegenov K. I., Krivykh V. V., Chudin O. S., Smol’yakov A. F., Dolgushin F., Semeikin O. V., Shteltser N. A., Ustynyuk N. A. Adducts of Mn and Re vinylidenes with P–OR nucleophiles: Hydrolysis rather than the intramolecular Michaelis–Arbuzov rearrangement // Journal of Organometallic Chemistry. 2018. Vol. 867. pp. 113-124.
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TY - JOUR
DO - 10.1016/j.jorganchem.2017.10.008
UR - https://doi.org/10.1016/j.jorganchem.2017.10.008
TI - Adducts of Mn and Re vinylidenes with P–OR nucleophiles: Hydrolysis rather than the intramolecular Michaelis–Arbuzov rearrangement
T2 - Journal of Organometallic Chemistry
AU - Utegenov, Kamil I
AU - Krivykh, Vasily V
AU - Chudin, Oleg S.
AU - Smol’yakov, Alexander F.
AU - Dolgushin, Fedor
AU - Semeikin, Oleg V.
AU - Shteltser, Nikolai A
AU - Ustynyuk, N. A.
PY - 2018
DA - 2018/07/01
PB - Elsevier
SP - 113-124
VL - 867
SN - 0022-328X
SN - 1872-8561
ER -
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@article{2018_Utegenov,
author = {Kamil I Utegenov and Vasily V Krivykh and Oleg S. Chudin and Alexander F. Smol’yakov and Fedor Dolgushin and Oleg V. Semeikin and Nikolai A Shteltser and N. A. Ustynyuk},
title = {Adducts of Mn and Re vinylidenes with P–OR nucleophiles: Hydrolysis rather than the intramolecular Michaelis–Arbuzov rearrangement},
journal = {Journal of Organometallic Chemistry},
year = {2018},
volume = {867},
publisher = {Elsevier},
month = {jul},
url = {https://doi.org/10.1016/j.jorganchem.2017.10.008},
pages = {113--124},
doi = {10.1016/j.jorganchem.2017.10.008}
}
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