Preparation of cyclopentadienes and diazocyclopentadienesvia cyclopentenolones and cyclopentenones

Freeman, Brian H.; Gagan, J. M. F.; Lloyd, Douglas R.

doi:10.1016/0040-4020(73)80276-5

Cited by 11 publications

(3 citation statements)

References 18 publications

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“…MS data were obtained by EI; all samples were measured at 70 eV and 295 8C unless otherwise stated. Substituted cyclopentadienes 11 a, [20] 11 b, [21] and 13 [22] were prepared according to or in analogy to published procedures.…”

Section: Methodsmentioning

confidence: 99%

Palladium-Catalyzed Arylation of Cyclopentadienes

Dyker¹,

Heiermann²,

Miura

et al. 2000

Chem. Eur. J.

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Cyclopentadiene and metallocenes, typically zirconocene dichloride, are suitable substrates for multiple arylations with aryl bromides in palladium-catalyzed reactions. Thus, various aryl bromides bearing either an electron-donating or an electron-withdrawing substituent can react with these substrates to afford the corresponding 1,2,3,4,5-pentaaryl-1,3-cyclopentadienes in a single preparative step. Derivatives of cyclopentadiene, including di- and trisubstituted cyclopentadienes, and indene are arylated in a similar fashion.

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Section: Methodsmentioning

confidence: 99%

Palladium-Catalyzed Arylation of Cyclopentadienes

Dyker¹,

Heiermann²,

Miura

et al. 2000

Chem. Eur. J.

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“…Grubbs and co-workers prepared cyclopentadiene-functionalized styrene divinylbenzene copolymers by the two routes shown in Scheme . , Cyclopentadienes can be prepared from the reaction of cyclopentenones with organolithium or Grignard reagents followed by an acid catalyzed dehydration. , Grubbs and co-workers used this to synthesize a cyclopentadiene-functionalized styrene–divinylbenzene copolymer . Bromination followed by lithium–halogen exchange led to the lithiation of the styrene rings in the copolymer.…”

Section: Polymer Chemistry With Cyclopentadienementioning

confidence: 99%

Click Chemistry with Cyclopentadiene

Levandowski

Raines

2021

Chem. Rev.

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Cyclopentadiene is one of the most reactive dienes in normal electron-demand Diels–Alder reactions. The high reactivities and yields of cyclopentadiene cycloadditions make them ideal as click reactions. In this review, we discuss the history of the cyclopentadiene cycloaddition as well as applications of cyclopentadiene click reactions. Our emphasis is on experimental and theoretical studies on the reactivity and stability of cyclopentadiene and cyclopentadiene derivatives.

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“…Reactions of benzil with excess pentan-2-one (R = Et) and octan-2-one (R = C 5 H 11 ) and a small amount of concentrated alkali led to formation of mixtures of isomers I-III [2][3][4]6] which can readily be distinguished by 1 H NMR spectroscopy. When the reactions of benzil with pentan-2-one and heptan-2-one were carried out in dilute solution, only one isomer I (R = Et, Bu) was obtained [5].…”

mentioning

confidence: 99%

Structure of 2(5)-alkyl-4-hydroxy-3,4-diphenylcyclopent-2-en-1-ones, cyclocondensation products of benzil with aliphatic ketones

2010

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The reaction of benzil with methyl alkyl ketones gave three isomeric cyclopentenone derivatives, 2-substituted and cis-and trans-5-substituted 4-hydroxy-3,4-diphenylcyclopent-2-en-1-ones. cis-and trans-2,5-Disubstituted 4-hydroxy-3,4-diphenylcyclopent-2-en-1-ones were formed in analogous reaction of benzil with dialkyl ketones. The structure of the products was confirmed by 1 H NMR spectroscopy and molecularmechanics calculations.

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Preparation of cyclopentadienes and diazocyclopentadienesvia cyclopentenolones and cyclopentenones

Cited by 11 publications

References 18 publications

Palladium-Catalyzed Arylation of Cyclopentadienes

Palladium-Catalyzed Arylation of Cyclopentadienes

Click Chemistry with Cyclopentadiene

Structure of 2(5)-alkyl-4-hydroxy-3,4-diphenylcyclopent-2-en-1-ones, cyclocondensation products of benzil with aliphatic ketones

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