Nitrosochlorination of Alkenes

Kadzyauskas, P. P.; Зефиров, Н. С.

doi:10.1070/rc1968v037n07abeh001665

Cited by 41 publications

(16 citation statements)

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“…[3][4][5][6] Over the last two decades, the use of solid supports in synthetic chemistry has become popular and in recent years the use of supported reagents under solvent-free conditions has opened up new and surprisingly useful approaches to chemistry. 7 Among oxidants, supported potassium permanganate has proven to be a reagent whose reactions are easily adapted to solvent-free conditions.…”

Section: Methodsmentioning

confidence: 99%

Cleavage of Oximes, Semicarbazones, and Phenylhydrazones with Supported Potassium Permanganate

Shaabani¹,

Naderi²,

Rahmati³

et al. 2005

Synthesis

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Potassium permanganate supported on manganese(II) sulfate or activated manganese dioxide can be used effectively for the oxidative cleavage of oximes and semicarbazones under solvent-free conditions and for the cleavage of phenylhydrazones in dichloromethane. The residue that remains after extraction of the organic products, primarily manganese oxides, can be recycled, making the process, in theory, infinitely sustainable.

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Section: Methodsmentioning

confidence: 99%

Cleavage of Oximes, Semicarbazones, and Phenylhydrazones with Supported Potassium Permanganate

Shaabani¹,

Naderi²,

Rahmati³

et al. 2005

Synthesis

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“…The latter route is possible if the carbon atom bound to the nitroso group carries a hydrogen atom (Scheme 1). 24,25 The reactions with ordinary alkenes can be classified as electrophilic substitution, and the adduct is formed in conformity with the Markovnikov rule. 24,25 The fact that nitrosyl chloride adds unexpectedly rapidly to some a,b-unsaturated carbonyl compounds 27 ± 29 might be due to preliminary coordination of the nitrosonium cation (NO + ) to the oxygen atom of the carbonyl group.…”

Section: 14-elimination In a A-substituted Oximes Under The Actionmentioning

confidence: 98%

Conjugated nitrosoalkenes

Lyapkalo¹,

Ioffe²

1998

Russ. Chem. Rev.

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Published data on the preparation, structure, physical and chemical properties, and reactivity of nitrosoalkenes are described systematically. The influence of the structure and stereoelectronic effects of substituents at the double bond on the stability of nitrosoalkenes is analysed. Primary attention is paid to concerted cycloaddition of nitrosoalkenes to miscellaneous multiple bonds, in particular, to the problems of regio-, stereo-, and enantioselectivity of [4 + 2]-cycloaddition of nitrosoalkenes to alkenes. The bibliography includes 183 references.

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“…Mechanistically, the formation of the 1,2-dichloro-1-nitroso compounds 1c-5c is also possible by the reaction of NOCl with 1-chlorocycloalkenes, 7 which can in principle be formed as intermediates from the primary adducts of reaction as depicted in Scheme 7. …”

Section: Methodsmentioning

confidence: 99%

Nitrosyl chloride addition to cycloalkenyltrimethylsilanes. An unexpected reversal of regiochemistry of addition, and synthesis of β-aminosilanes

Mallya¹,

Nagendrappa²

2007

Arkivoc

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Cycloalkenyltrimethylsilanes add nitrosyl chloride stereo-and regio-selectively. The addition is syn, with chlorine and nitrosyl group adding to C-1 and C-2 respectively. The products dimerize to diazene dioxides, whose stability depends on the conformational flexibility of the ring -the less flexible are more stable. The less stable adducts convert to oximes and further to 1,2-dichloro-1-nitrosocycloalkanes. The adducts can be hydrolysed to α-chloroketones and reduced to β-aminosilanes. Other interesting observations include transposition of keto group in α-chloroketones and X-ray crystal structure of the amide derivative 6f, which reveals -(CO)-HN…H-CH 2 -(CO)-hydrogen contact.

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Nitrosochlorination of Alkenes

Cited by 41 publications

References 0 publications

Cleavage of Oximes, Semicarbazones, and Phenylhydrazones with Supported Potassium Permanganate

Cleavage of Oximes, Semicarbazones, and Phenylhydrazones with Supported Potassium Permanganate

Conjugated nitrosoalkenes

Nitrosyl chloride addition to cycloalkenyltrimethylsilanes. An unexpected reversal of regiochemistry of addition, and synthesis of β-aminosilanes

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