On the regioselectivity of alkylation of the (trimethylsilyl) tetramethylcyclopentadienide anion. A new approach to the synthesis of 1,2,3,4-tetramethylfulvene
Publication type: Journal Article
Publication date: 2004-10-01
scimago Q3
SJR: 0.305
CiteScore: 2.8
Impact factor: —
ISSN: 10665285, 15739171
General Chemistry
Abstract
The regioselectivity of alkylation of lithium (trimethylsilyl)tetramethylcyclopentadienide C5Me4SiMe3 −Li+ was studied by 1H and 13C NMR spectroscopy using its reactions with MeI, MeOTs, ClCH2CH2Br, and ClCH2CH2I in different solvents as representative examples. Sterically non-hindered MeI and MeOTs presumably attack the C atom bonded to the silyl group giving 1,2,3,4,5-pentamethylcyclopentadienylsilane. For bulkier alkyl halides, such as ClCH2CH2Br and ClCH2CH2I, the regioselectivity of alkylation changes to form preferentially gem-dialkyl-substituted cyclopentadienes. The reaction of C5Me4SiMe3 −Li+ with formaldehyde affords 1,2,3,4-tetramethylfulvene in a high yield, providing an alternative synthetic approach to a number of ω-functionalized peralkylated cyclopentadienes. The quantum-chemical calculations of the C5Me4SiMe3 − anion by the RHF and DFT (RMPW1PW91) methods in the valence-split 6-311+G(d,p) basis set are in good agreement with the experimental data.
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Krutko D. P., Borzov M. V., Veksler E. N. On the regioselectivity of alkylation of the (trimethylsilyl) tetramethylcyclopentadienide anion. A new approach to the synthesis of 1,2,3,4-tetramethylfulvene // Russian Chemical Bulletin. 2004. Vol. 53. No. 10. pp. 2182-2186.
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Krutko D. P., Borzov M. V., Veksler E. N. On the regioselectivity of alkylation of the (trimethylsilyl) tetramethylcyclopentadienide anion. A new approach to the synthesis of 1,2,3,4-tetramethylfulvene // Russian Chemical Bulletin. 2004. Vol. 53. No. 10. pp. 2182-2186.
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TY - JOUR
DO - 10.1007/s11172-005-0095-9
UR - https://doi.org/10.1007/s11172-005-0095-9
TI - On the regioselectivity of alkylation of the (trimethylsilyl) tetramethylcyclopentadienide anion. A new approach to the synthesis of 1,2,3,4-tetramethylfulvene
T2 - Russian Chemical Bulletin
AU - Krutko, D P
AU - Borzov, M V
AU - Veksler, E N
PY - 2004
DA - 2004/10/01
PB - Springer Nature
SP - 2182-2186
IS - 10
VL - 53
SN - 1066-5285
SN - 1573-9171
ER -
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@article{2004_Krutko,
author = {D P Krutko and M V Borzov and E N Veksler},
title = {On the regioselectivity of alkylation of the (trimethylsilyl) tetramethylcyclopentadienide anion. A new approach to the synthesis of 1,2,3,4-tetramethylfulvene},
journal = {Russian Chemical Bulletin},
year = {2004},
volume = {53},
publisher = {Springer Nature},
month = {oct},
url = {https://doi.org/10.1007/s11172-005-0095-9},
number = {10},
pages = {2182--2186},
doi = {10.1007/s11172-005-0095-9}
}
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Krutko, D. P., et al. “On the regioselectivity of alkylation of the (trimethylsilyl) tetramethylcyclopentadienide anion. A new approach to the synthesis of 1,2,3,4-tetramethylfulvene.” Russian Chemical Bulletin, vol. 53, no. 10, Oct. 2004, pp. 2182-2186. https://doi.org/10.1007/s11172-005-0095-9.
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