Dendralenes - Citizendia

Dendralenes are discrete acyclic cross-conjugated polyenes. Cross-conjugation is a special type of conjugation in a Molecule, when in a set of three Pi bonds only two pi-bonds interact with each other by conjugation Polyenes are poly- unsaturated Organic compounds that contain one or more sequences of alternating double and single Carbon -carbon bonds The simplest dendralene is butadiene (1) or [2]dendralene followed by [3]dendralene (2), [4]dendralene (3) and [5]dendralene (4) and so forth.

The name dendralene is pulled together from the words dendrimer, linear and alkene. Dendrimers are repeatedly branched Molecules The huge number of papers on dendritic architectures such as dendrimers dendronized hyperbranched and brush-polymers has generated The word linear comes from the Latin word linearis, which means created by lines. In Organic chemistry, an alkene, olefin, or olefine is an unsaturated Chemical compound containing at least one Carbon The higher dendralenes are of scientific interest because they open up a large array of new organic compounds from a relatively simple precursor especially by Diels-Alder chemistry. An organic compound is any member of a large class of Chemical compounds whose Molecules contain Carbon. The Diels-Alder reaction is an Organic chemical reaction (specifically a Cycloaddition) between a conjugated Diene and a substituted Alkene, Their cyclic counterparts are aptly called radialenes. Radialenes are Alicyclic Organic compounds containing n cross-conjugated Exocyclic Double bonds The double bonds are commonly

One synthetic route to [4]dendralene starts from chloroprene. Organic synthesis is a special branch of Chemical synthesis and is concerned with the construction of Organic compounds via Organic reactions Organic Chloroprene is the common name for the Organic compound 2-chloro-13-butadiene, which has the Chemical formula CH2=CCl-CH=CH2 ^[1] This compound is converted to a Grignard reagent by action of magnesium metal which is then reacted with copper(I) chloride to an organocopper intermediate which is in turn dimerized in an oxidative coupling reaction to the butadiene dimer with copper(II) chloride. The Grignard reaction, named for the French chemist François Auguste Victor Grignard, is an organometallic Chemical reaction in which Alkyl - Magnesium (mægˈniːziəm is a Chemical element with the symbol Mg, Atomic number 12 Atomic weight 24 Copper(I chloride, commonly called cuprous chloride is the lower Chloride of Copper, with the formula CuCl Organocopper compounds in Organometallic chemistry contain Carbon to Copper Chemical bonds Organocopper chemistry is the science of A coupling reaction or oxidative coupling in Organic chemistry is a catch-all for a range of reactions in organometallic chemistry where two Hydrocarbon A dimer is a Chemical or Biological entity consisting of two subunits called Monomers which are held together by either Intramolecular forces Copper(II chloride is the Chemical compound with the formula CuCl2

[4]dendralene synthetic scheme from chloroprene

Diels-Alder reactions

[4]dendralene shows a tandem Diels-Alder reaction with the dienophile N-methyl-maleimide or NMM. A cascade reaction or tandem reaction or domino reaction is a consecutive series of Intramolecular Organic reactions which often proceed via highly The Diels-Alder reaction is an Organic chemical reaction (specifically a Cycloaddition) between a conjugated Diene and a substituted Alkene, The Diels-Alder reaction is an Organic chemical reaction (specifically a Cycloaddition) between a conjugated Diene and a substituted Alkene, Maleimide is the Chemical compound with the formula H2C2(CO2NH Complete site selectivity is possible with the addition of the lewis acid methyldichloroaluminium. With one set of premixing and 2 equivalents of NMM the central diene group is targeted to the monoadduct 3. With another set and a larger amount of dienophile the terminal groups react and the reaction proceeds from the monoadduct to the trisadducts 2 and 2b.

References

^ Alan D. Payne, Anthony C. Willis, and Michael S. Sherburn (2005). "Practical Synthesis and Diels-Alder Chemistry of [4]Dendralene". Journal of the American Chemical Society 127 (35): 12188–12189. doi:10.1021/ja053772. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document.