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Cyclopentenone also functions as an excellent dienophile in the Diels–Alder reaction, reacting with a wide variety of dienes. In one example, a Danishefsky-type diene is reacted with a cyclopentenone to yield a fused tricyclic system en route to the synthesis of coriolin. [6] Cyclopentenone in the synthesis of coriolin
Ketene cycloadditions proceed by a concerted, [2+2] cycloaddition mechanism. Ketenes, unlike most alkenes, can align antarafacially with respect to other alkenes. Thus, the suprafacial- antarafacial geometry required for concerted, thermal [2+2] cycloaddition can be achieved in reactions of ketenes. [4]
1,3-Cyclopentanedione is an organic compound with the formula (CH 2) 3 (CO) 2. It is one of two isomeric cyclopentanediones, the other being 1,2-cyclopentanedione . The enol is predicted to be about 1-3 kcal/mol more stable than the diketo form. [ 1 ]
1,2-Cyclopentanedione is the organic compound with the formula (CH 2) 3 (CO) 2.It is one of two isomeric cyclopentanediones, the other being 1,3-cyclopentanedione.It was first prepared by base-induced condensation of di ethylglutarate with diethyloxalate, followed by hydrolysis of the resulting diketodiester followed by decarboxylation. [1]
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 ...
One example of a formal [3+3]cycloaddition between a cyclic enone and an enamine catalyzed by n-butyllithium is a Stork enamine / 1,2-addition cascade reaction: [7] An intermolecular formal [3+3] cycloaddition between an cyclic iminium chloride and cyclopentenone.
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Cyclopentadienone is an organic compound with molecular formula C 5 H 4 O. The parent cyclopentadienone is rarely encountered, because it rapidly dimerizes. [1] Many substituted derivatives are known, notably tetraphenylcyclopentadienone.