Electrochemically induced oxidative rearrangement of alkylidenemalonates
Publication type: Journal Article
Publication date: 1998-11-01
scimago Q3
wos Q2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
Alkylidenemalonates capable of double bond migration being electrolyzed in methanol or ethanol in the presence of alkali metal halides in an undivided cell equipped with Fe cathode are transformed into 2-alkyl-3,3-dimethoxyalkane-1,1-dicarboxylates in 70–90% yield via electrochemically induced oxidative rearrangement. Acidification of the reaction mixture after the electrolysis leads to the formation of 2-alkyl-3-oxoalkane-1,1-dicarboxylates. In the case of isobutylidenemalonate, the electrolysis intermediate dimethyl 3,3-dimethyl-2-methoxy-cyclopropane-1,1-dicarboxylate was isolated in 70% yield.
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Elinson M. N., Feducovich S. K., Nikishin G. I. Electrochemically induced oxidative rearrangement of alkylidenemalonates // Tetrahedron. 1998. Vol. 54. No. 48. pp. 14529-14540.
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Elinson M. N., Feducovich S. K., Nikishin G. I. Electrochemically induced oxidative rearrangement of alkylidenemalonates // Tetrahedron. 1998. Vol. 54. No. 48. pp. 14529-14540.
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TY - JOUR
DO - 10.1016/s0040-4020(98)00912-0
UR - https://doi.org/10.1016/s0040-4020(98)00912-0
TI - Electrochemically induced oxidative rearrangement of alkylidenemalonates
T2 - Tetrahedron
AU - Elinson, M. N.
AU - Feducovich, Sergey K.
AU - Nikishin, Gennady I.
PY - 1998
DA - 1998/11/01
PB - Elsevier
SP - 14529-14540
IS - 48
VL - 54
SN - 0040-4020
SN - 1464-5416
ER -
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BibTex (up to 50 authors)
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@article{1998_Elinson,
author = {M. N. Elinson and Sergey K. Feducovich and Gennady I. Nikishin},
title = {Electrochemically induced oxidative rearrangement of alkylidenemalonates},
journal = {Tetrahedron},
year = {1998},
volume = {54},
publisher = {Elsevier},
month = {nov},
url = {https://doi.org/10.1016/s0040-4020(98)00912-0},
number = {48},
pages = {14529--14540},
doi = {10.1016/s0040-4020(98)00912-0}
}
Cite this
MLA
Copy
Elinson, M. N., et al. “Electrochemically induced oxidative rearrangement of alkylidenemalonates.” Tetrahedron, vol. 54, no. 48, Nov. 1998, pp. 14529-14540. https://doi.org/10.1016/s0040-4020(98)00912-0.