Phosphonium salts derived from Α-ferrocenylvinyl cation in situ generated in sc-CO2 from ethynylferrocene by Nafion film
Тип публикации: Journal Article
Дата публикации: 2018-01-01
scimago Q1
wos Q2
БС1
SJR: 0.757
CiteScore: 7.8
Impact factor: 4.4
ISSN: 08968446, 18728162
Physical and Theoretical Chemistry
General Chemical Engineering
Condensed Matter Physics
Краткое описание
A superacidic polymer Nafion protonates ferrocenylacetylene (1) in sc−CO2 (35 °C, 9 MPa) to from the α-ferrocenylvinyl cation, FcC+=CH2 (2, Fc = ferrocenyl). Carbocation 2 in situ alkenylates dimethyl sulfide (25 MPa) or 1,4-dithiane (35 MPa) to give 1-ferrocenylvinyl sulfonium salts isolated as the tetrafluoroborates: [Me2S+C(Fc)=CH2]BF4− (3, 85%), cis- [R2S+C(Fc)=CH2]BF4− (R2 = CH2CH2SCH2CH2) (4, 31%) and trans-[R2S+CH = CH(Fc)]BF4− (5, 91%). Salt 5 is the isomer of compound 4 resulting from the 1,4-dithiane ring shift from α- to β- position to the Fc group. Salt 5 undergoes S+–C bond scission on the action of HN(i-Pr)2 affording the neutral diene trans-FcCH = CHSCH2CH2SCH = CH2 (6, 89%). Complexes 4-6 were fully characterized by the NMR spectra data. The molecular structures of 4 and 5 were elucidated by X-ray study.
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Journal of Supercritical Fluids
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Moiseev S. K. et al. Phosphonium salts derived from Α-ferrocenylvinyl cation in situ generated in sc-CO2 from ethynylferrocene by Nafion film // Journal of Supercritical Fluids. 2018. Vol. 131. pp. 117-123.
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Kizas O. A., Moiseev S. K., Chaschin I. S., Godovikov I. A., Dolgushin F., Nikolaev A. Yu., Nikitin L. N., Khokhlov A. R. Phosphonium salts derived from Α-ferrocenylvinyl cation in situ generated in sc-CO2 from ethynylferrocene by Nafion film // Journal of Supercritical Fluids. 2018. Vol. 131. pp. 117-123.
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TY - JOUR
DO - 10.1016/j.supflu.2017.09.005
UR - https://doi.org/10.1016/j.supflu.2017.09.005
TI - Phosphonium salts derived from Α-ferrocenylvinyl cation in situ generated in sc-CO2 from ethynylferrocene by Nafion film
T2 - Journal of Supercritical Fluids
AU - Kizas, O A
AU - Moiseev, S K
AU - Chaschin, I S
AU - Godovikov, I A
AU - Dolgushin, F.M.
AU - Nikolaev, A Yu
AU - Nikitin, L. N.
AU - Khokhlov, A R
PY - 2018
DA - 2018/01/01
PB - Elsevier
SP - 117-123
VL - 131
SN - 0896-8446
SN - 1872-8162
ER -
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@article{2018_Moiseev,
author = {O A Kizas and S K Moiseev and I S Chaschin and I A Godovikov and F.M. Dolgushin and A Yu Nikolaev and L. N. Nikitin and A R Khokhlov},
title = {Phosphonium salts derived from Α-ferrocenylvinyl cation in situ generated in sc-CO2 from ethynylferrocene by Nafion film},
journal = {Journal of Supercritical Fluids},
year = {2018},
volume = {131},
publisher = {Elsevier},
month = {jan},
url = {https://doi.org/10.1016/j.supflu.2017.09.005},
pages = {117--123},
doi = {10.1016/j.supflu.2017.09.005}
}