Radical cyclisation of 2,6-dinitroalkanes

Bowman, W. Russell; Jackson, Stuart W.

doi:10.1016/s0040-4039(00)99598-4

Cited by 13 publications

(4 citation statements)

References 5 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This method is based upon a recent report detailing the ferricyanide-mediated intramolecular coupling of acyclic 1,5-dinitronates to yield vicinal dinitrocyclopentanes . The dl/meso -2,6-dinitroheptane was successfully cyclized to a mixture of isomeric 1,2-dimethyl-1,2-dinitrocyclopentanes, in accordance with the published report 16b. However, this method did not result in cyclization for any of the other substrates obtained from the above dioxime oxidations.…”

Section: Resultssupporting

confidence: 73%

“…The availability of the uncyclized dinitro derivatives from a number of the oxime oxidations ( vide supra ) afforded the serendipitous opportunity to investigate an alternative cyclization strategy. This method is based upon a recent report detailing the ferricyanide-mediated intramolecular coupling of acyclic 1,5-dinitronates to yield vicinal dinitrocyclopentanes . The dl/meso -2,6-dinitroheptane was successfully cyclized to a mixture of isomeric 1,2-dimethyl-1,2-dinitrocyclopentanes, in accordance with the published report 16b.…”

Section: Resultsmentioning

confidence: 60%

“…The scope of the oxidative cyclization was further investigated using a number of readily available dioximes. It was determined that the dioximes of cis -bicyclo[3.3.0]octane-3,7-dione, 2,6-heptanedione, 1,4-cyclohexanedione, and 2,5-hexanedione were oxidized but failed to cyclize and yielded instead the corresponding dinitro compounds 3,7-dinitro- cis -bicyclo[3.3.0]octane, dl/meso 2,6-dinitroheptane,16b 1,4-dinitrocyclohexane, and dl/meso -2,5-dinitrohexane 16b in 51%, 50%, 50%, and 10% yields, respectively. The yields of the oxime oxidations were modest due to the formation of significant amounts of ketone and/or lactone byproducts.…”

Section: Resultsmentioning

confidence: 99%

“…2,5-Dinitrohexane. 16b The bisoxime of 2,5-hexanedione was subjected to the reaction conditions of method A ( vide supra ). A 10% yield of 2,5-dinitrohexane, as a mixture of dl and meso stereoisomers was obtained following PLC ( R f = 0.88; silica gel, CHCl 3 ).…”

Section: Methodsmentioning

confidence: 99%

See 3 more Smart Citations

Oxidative Intramolecular Cyclization of Diketoximes: Synthesis of 1,5-Dinitro-cis-bicyclo[3.3.0]octane¹

et al. 1996

View full text Add to dashboard Cite

Section: Resultssupporting

confidence: 73%

Section: Resultsmentioning

confidence: 60%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

See 2 more Smart Citations

Oxidative Intramolecular Cyclization of Diketoximes: Synthesis of 1,5-Dinitro-cis-bicyclo[3.3.0]octane¹

et al. 1996

View full text Add to dashboard Cite

Radical Cyclization Reactions

et al. 1996

View full text Add to dashboard Cite

Radical cyclization reactions are among the most powerful and versatile methods for the construction of mono‐ and polycyclic systems. The advantages these reactions offer to the synthetic organic chemist include high functional group tolerance and mild reaction conditions combined with high levels of regio‐ and stereochemistry. Furthermore, the recent progress in radical chemistry has led to the development of a broad range of very useful practical methods to conduct radical cyclization reactions. In general, radical cyclization reactions comprise three basic steps: selective radical generation, radical cyclization, and conversion of the cyclized radical to the product. For the generation of the initial radical a broad variety of suitable precursors can be employed, such as halides, thio‐ and selenoethers, alcohols, aldehydes and hydrocarbons. The cyclization step usually involves the intramolecular addition of a radical to a multiple bond. Most often carbon–carbon multiple bonds are employed; however, there are also examples known for the addition to carbon–oxygen and carbon–nitrogen bonds. Depending on the method employed, the cyclized radical is converted to the desired product by trapping with a radical scavenger, by a fragmentation reaction, or by an electron transfer reaction. The section Mechanism, Regio‐ and Stereochemistry provides an introduction to the key features of radical cyclization with a special emphasis on the factors controlling the regio‐ and stereochemistry. The section Scope and Limitations covers the different methods used to conduct radical cyclization. The basic principles of radical chemistry and general practical considerations when conducting radical cyclizations are not discussed in detail. Several excellent review articles and books dealing with these topics are available.

show abstract

ChemInform Abstract: Radical Cyclization of 2,6‐Dinitroalkanes.

Bowman

Jackson

1989

ChemInform

View full text Add to dashboard Cite

Radical cyclisation of 2,6-dinitroalkanes

Cited by 13 publications

References 5 publications

Oxidative Intramolecular Cyclization of Diketoximes: Synthesis of 1,5-Dinitro-cis-bicyclo[3.3.0]octane¹

Oxidative Intramolecular Cyclization of Diketoximes: Synthesis of 1,5-Dinitro-cis-bicyclo[3.3.0]octane¹

Radical Cyclization Reactions

ChemInform Abstract: Radical Cyclization of 2,6‐Dinitroalkanes.

Contact Info

Product

Resources

About

Radical cyclisation of 2,6-dinitroalkanes

Cited by 13 publications

References 5 publications

Oxidative Intramolecular Cyclization of Diketoximes: Synthesis of 1,5-Dinitro-cis-bicyclo[3.3.0]octane1

Oxidative Intramolecular Cyclization of Diketoximes: Synthesis of 1,5-Dinitro-cis-bicyclo[3.3.0]octane1

Radical Cyclization Reactions

ChemInform Abstract: Radical Cyclization of 2,6‐Dinitroalkanes.

Contact Info

Product

Resources

About

Oxidative Intramolecular Cyclization of Diketoximes: Synthesis of 1,5-Dinitro-cis-bicyclo[3.3.0]octane¹

Oxidative Intramolecular Cyclization of Diketoximes: Synthesis of 1,5-Dinitro-cis-bicyclo[3.3.0]octane¹