Electrochemical-Chemical Synthesis of Methylene bis(Aluminum Dichloride)

Mottus, Edward H.; Ort, Morris R.

doi:10.1149/1.2407663

Cited by 17 publications

(2 citation statements)

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“…Dichloromethane 20, on electroreduction, gen-erates the carbene with loss of two chloride ions, which on treatment with ethylene 21 affords the expected cyclopropane 22. [18] In 1972, Fry and co-workers also reported electrochemical cyclopropanation of geminal dihalonorbornanes 23 to produce nortricyclene 24 in addition to the monohalogenated product (endo-norbornyl halide) using platinum and mercury cathodes (Scheme 7). [19] Later in 1991, Sibille et al, published a detailed report on the electrochemical synthesis of cyclopropane derivatives 27 using a wide variety of alkenes 25 with dihalomethanes 26.…”

Section: Electroreductive Cyclopropanationmentioning

confidence: 99%

“…reported the formation of cyclopropane by electrolysis of dichloromethane on aluminium anode in an undivided cell. Dichloromethane 20 , on electroreduction, generates the carbene with loss of two chloride ions, which on treatment with ethylene 21 affords the expected cyclopropane 22 [18] . In 1972, Fry and co‐workers also reported electrochemical cyclopropanation of geminal dihalonorbornanes 23 to produce nortricyclene 24 in addition to the monohalogenated product ( endo ‐norbornyl halide) using platinum and mercury cathodes (Scheme 7).…”

Section: Electrochemical Synthesis Of Cyclopropanementioning

confidence: 99%

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Electrochemical Synthesis and Reactivity of Three‐Membered Strained Carbo‐ and Heterocycles

Kumar

Banerjee

Kumar

et al. 2023

Chemistry A European J

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Three‐membered carbocyclic‐ and heterocyclic ring structures are versatile synthetic building blocks in organic synthesis owing to their biological importance. Also, the inherent strain of these three‐membered rings led to their ring‐opening functionalization via C‐C, C‐N, and C‐O bond cleavage. Traditional synthesis and ring‐opening methods of these molecules require the usage of acid catalysts or transition‐metals. Recently, electroorganic synthesis has emerged as a powerful tool for initiating new chemical transformations. In this review, the synthetic and mechanistic aspects of electro‐mediated synthesis and ring‐opening functionalization of three‐membered carbo‐ and heterocycles are highlighted.

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Section: Electroreductive Cyclopropanationmentioning

confidence: 99%

Section: Electrochemical Synthesis Of Cyclopropanementioning

confidence: 99%

Electrochemical Synthesis and Reactivity of Three‐Membered Strained Carbo‐ and Heterocycles

Kumar

Banerjee

Kumar

et al. 2023

Chemistry A European J

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The Chemistry of Bis‐Aluminated Compounds

Matsubara

2016

Patai's Chemistry of Functional Groups

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In this chapter, representative examples of bis‐aluminated compound chemistry will be shown. The compounds can be classified roughly into two categories: The preparations and reactions of gem ‐dialuminated compounds will be discussed first, followed by those of aluminacycles. They have been expected to work as a dianion equivalent in organic syntheses, and have actually shown specific molecular transformations taking advantage of their capabilities. Although they possess a dianionic character, they have reasonable stability. As useful reactions of gem ‐dialuminated compounds, alkylidenation of carbonyl compounds and subsequential reactions with electrophiles will be shown. In addition, preparation of cyclic compounds via an insertion reaction of electrophiles into aluminacyles will be discussed.

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