CuCl-Catalyzed ring-opening isomerization of gem-chlorofluorocyclopropanes with the formation of chlorofluoroalkenes and chlorofluoroalkadienes

Novikov, Maxim A.; Volchkov, N. V.; Lipkind, M. B.; Нефедов, О. М.

doi:10.1007/s11172-013-0009-1

Cited by 13 publications

(5 citation statements)

References 30 publications

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“…In 2013, they reported the Cu(I)-catalyzed opening of gem-chlorofluorocyclopropanes in the presence of a catalytic amount of CuCl to give the corresponding allylic 3-chloro-2-fluoroalk-1-enes (Scheme 73). 17,18 In 2015, Novikov, Volchkov, and co-workers reported the copper-catalyzed solvolysis of gem-bromofluorocyclopropanes and gem-chlorofluorocyclopropanes. 19 2-Fluoroallyl methyl ethers, esters and alcohols were obtained by…”

Section: Scheme 72 Ni-catalyzed Ring-opening Of Gem-difluorocyclopropmentioning

confidence: 99%

“…As part of their work on the copper-catalyzed ringopening isomerization of gem-chlorofluorocyclopropanes (see Scheme 7, Section 2.1.3.1), Volchkov and co-workers prepared tetrasubstituted fluoroalkenes (Scheme 222). 17,18 Fluorodienes prepared by this methodology, such as from 1-chloro-1-fluoro-2-methyl-2-vinylcyclopropane, underwent a subsequent cycloaddition reaction if N-phenylmaleimide was present in the reaction flask (Scheme 223). 18…”

Section: Ring-opening Reactions Of Gem-dihalocyclopropanes 431 Tranmentioning

confidence: 99%

“…17,18 Fluorodienes prepared by this methodology, such as from 1-chloro-1-fluoro-2-methyl-2-vinylcyclopropane, underwent a subsequent cycloaddition reaction if N-phenylmaleimide was present in the reaction flask (Scheme 223). 18…”

Section: Ring-opening Reactions Of Gem-dihalocyclopropanes 431 Tranmentioning

confidence: 99%

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Synthesis of Monofluoroalkenes: A Leap Forward

2018

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Monofluoroalkenes have found wide application in organic chemistry, medicinal chemistry, and materials science. This review summarizes the most recent advances made regarding the preparation of monofluoroalkenes, covering the period between October 2010 and September 2017. This review is divided in three main parts, one for each possible substitution pattern, namely di-, tri-, and tetrasubstituted. Then, for each class, further subclassification is made according to the reaction type.1 Introduction2 Disubstituted Monofluoroalkenes2.1 Disubstituted α-Monofluoroalkenes2.2 Disubstituted β-Monofluoroalkenes3 Trisubstituted Monofluoroalkenes4 Tetrasubstituted Monofluoroalkenes5 Conclusions

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Section: Scheme 72 Ni-catalyzed Ring-opening Of Gem-difluorocyclopropmentioning

confidence: 99%

Section: Ring-opening Reactions Of Gem-dihalocyclopropanes 431 Tranmentioning

confidence: 99%

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Synthesis of Monofluoroalkenes: A Leap Forward

2018

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“…73 Cu(I)Cl catalyzed electrocyclic ring opening isomerization of gem-chlorofluorocyclopropanes 125 with phenyl-, vinyl-, alkyland cyclopropyl substituents is reported (Scheme 46). 74 The reaction when carried out in aprotic solvents led to the formation of Z-and E-chlorofluoroalkenes.…”

Section: Ring Opening/expansion Reactionsmentioning

confidence: 99%

Recent advances in the syntheses, transformations and applications of 1,1-dihalocyclopropanes

et al. 2015

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gem-Dihalocyclopropanes have wide-spread applications in organic synthesis due to their versatile chemistry. They can serve as substrates for a large range of useful materials such as natural products, alkaloids, cyclopropanes, heterocycles, aromatic ring systems etc. Normally the dihalocyclopropanes are prepared by the addition of dihalocarbene to alkene, but due to the great synthetic efficacy of gem-dihalocyclopropanes a number of methods have been developed for their synthesis. Generally gem-dihalocyclopropanes exist as strained cyclic systems with astonishing kinetic stability. They are capable of undergoing transformations leading to a variety of products which have potential applications in various synthetic organic chemistry fields.

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“…The subsequent rearrangement of the fluorochlorocyclopropane moiety can be induced not only by thermolysis (300 ± 500 8C) but also on moderate heating (80 8C) in the presence of a catalytic amount of copper(I) chloride or a CuCl and LiCl mixture in acetonitrile. 103,104 Scheme 20…”

Section: Scheme 19mentioning

confidence: 99%