Ionic Ga-Complexes of Alkylidene- and Arylmethylidenemalonates and Their Reactions with Acetylenes: An In-Depth Look into the Mechanism of the Occurring Gallium Chemistry
Тип публикации: Journal Article
Дата публикации: 2018-10-02
scimago Q1
wos Q1
БС1
SJR: 5.554
CiteScore: 22.5
Impact factor: 15.6
ISSN: 00027863, 15205126
PubMed ID:
30274511
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Краткое описание
A new synthetic concept was suggested in the chemistry of substituted methylidenemalonates that enables their utilization as 1,2-zwitterionic synthons. This strategy is to generate liquid ionic Ga complexes from methylidenemalonates and GaHal3 with a strict 3/4 composition and then use them in further synthesis. A number of complexes with different metal halides have been synthesized and studied in detail. The unique properties of gallium among all metals have been demonstrated and explained. On the basis of the discovered new class of gallium complexes of methylidenemalonates, a number of novel reactions with acetylenes have been elaborated, which are unknown in the conventional chemistry of methylidenemalonates. The main demonstrated process is a three-component addition to a triple bond involving halide anions, leading to the formation of polyfunctional vinyl halides with high E-selectivity. The mechanism has been studied experimentally in fine detail. Application of specially optimized 71Ga NMR spectroscopy makes it possible to take an in-depth look into the gallium chemistry in a new light. In particular, the key participation of GaHal4- anions in the occurring transformations has been established.
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Novikov R. G. et al. Ionic Ga-Complexes of Alkylidene- and Arylmethylidenemalonates and Their Reactions with Acetylenes: An In-Depth Look into the Mechanism of the Occurring Gallium Chemistry // Journal of the American Chemical Society. 2018. Vol. 140. No. 43. pp. 14381-14390.
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Novikov R. G., Denisov D. A., Potapov K. V., Tkachev Y. V., Shulishov E. V., Tomilov Y. V. Ionic Ga-Complexes of Alkylidene- and Arylmethylidenemalonates and Their Reactions with Acetylenes: An In-Depth Look into the Mechanism of the Occurring Gallium Chemistry // Journal of the American Chemical Society. 2018. Vol. 140. No. 43. pp. 14381-14390.
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TY - JOUR
DO - 10.1021/jacs.8b08913
UR - https://pubs.acs.org/doi/10.1021/jacs.8b08913
TI - Ionic Ga-Complexes of Alkylidene- and Arylmethylidenemalonates and Their Reactions with Acetylenes: An In-Depth Look into the Mechanism of the Occurring Gallium Chemistry
T2 - Journal of the American Chemical Society
AU - Novikov, Roman G.
AU - Denisov, Dmitry A
AU - Potapov, Konstantin V
AU - Tkachev, Yaroslav V.
AU - Shulishov, Evgeny V.
AU - Tomilov, Yury V.
PY - 2018
DA - 2018/10/02
PB - American Chemical Society (ACS)
SP - 14381-14390
IS - 43
VL - 140
PMID - 30274511
SN - 0002-7863
SN - 1520-5126
ER -
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@article{2018_Novikov,
author = {Roman G. Novikov and Dmitry A Denisov and Konstantin V Potapov and Yaroslav V. Tkachev and Evgeny V. Shulishov and Yury V. Tomilov},
title = {Ionic Ga-Complexes of Alkylidene- and Arylmethylidenemalonates and Their Reactions with Acetylenes: An In-Depth Look into the Mechanism of the Occurring Gallium Chemistry},
journal = {Journal of the American Chemical Society},
year = {2018},
volume = {140},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://pubs.acs.org/doi/10.1021/jacs.8b08913},
number = {43},
pages = {14381--14390},
doi = {10.1021/jacs.8b08913}
}
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MLA
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Novikov, Roman G., et al. “Ionic Ga-Complexes of Alkylidene- and Arylmethylidenemalonates and Their Reactions with Acetylenes: An In-Depth Look into the Mechanism of the Occurring Gallium Chemistry.” Journal of the American Chemical Society, vol. 140, no. 43, Oct. 2018, pp. 14381-14390. https://pubs.acs.org/doi/10.1021/jacs.8b08913.
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