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Cyclopentadiene is a highly reactive diene in the Diels–Alder reaction because minimal distortion of the diene is required to achieve the envelope geometry of the transition state compared to other dienes. [11] Famously, cyclopentadiene dimerizes. The conversion occurs in hours at room temperature, but the monomer can be stored for days at ...
Such a benzene derivative reacts with 1,7-octadiyne in the presence of a suitable catalyst to generate a naphthalene system. [15] This is an example of a hexadehydro Diels–Alder reaction . Trimerisation of three 2-butyne (dimethylacetylene) molecules yields hexamethylbenzene . [ 16 ]
The process, which is catalyzed by platinum supported by aluminium oxide, is exemplified in the conversion methylcyclohexane (a naphthene) into toluene (an aromatic). [2] Dehydrocyclization converts paraffins (acyclic hydrocarbons) into aromatics. [3] A related aromatization process includes dehydroisomerization of methylcyclopentane to benzene:
The retro-Diels–Alder reaction is used in the industrial production of cyclopentadiene. Cyclopentadiene is a precursor to various norbornenes, which are common monomers. The Diels–Alder reaction is also employed in the production of vitamin B6. Typical route for production of ethylidene norbornene from cyclopentadiene through vinyl ...
The core of the arene is a benzene ring and the periphery consists of alternating benzene rings (3) and cyclopentadiene rings (3). Unlike fullerene, sumanene has benzyl positions which are available for organic reactions.
The Sandmeyer reaction provides a method through which one can perform unique transformations on benzene, such as halogenation, cyanation, trifluoromethylation, and hydroxylation. The reaction was discovered in 1884 by Swiss chemist Traugott Sandmeyer , when he attempted to synthesize phenylacetylene from benzenediazonium chloride and copper(I ...
The main limitation of such approach, however, is the need to use constrained dienes, such as furan and cyclopentadiene. [14] In 2009 Buszek and co-workers synthesized herbindole A using aryne [4+2]-cycloaddition. [29] 6,7-indolyne undergoes [4+2] cycloaddition with cyclopentadiene to afford complex tetracyclic product.
1,2,3,4,5-Pentamethylcyclopentadiene is a cyclic diene with the formula C 5 (CH 3) 5 H, often written C 5 Me 5 H, where Me is CH 3. [3] It is a colorless liquid. [1]1,2,3,4,5-Pentamethylcyclopentadiene is the precursor to the ligand 1,2,3,4,5-pentamethylcyclopentadienyl, which is often denoted Cp* (C 5 Me 5) and read as "C P star", the "star" signifying the five methyl groups radiating from ...