Di-tert-butylcyclopentadiene and tri-tert-butylcyclopentadiene

Venier, Clifford G.; Casserly, Edward W.

doi:10.1021/ja00163a057

Cited by 75 publications

(39 citation statements)

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“…However, in these cases, the reaction proceeds by successive steps with a base necessary for the deprotonation of cyclopentadienes intermediates [16,17].…”

Section: Resultsmentioning

confidence: 99%

Optically active cyclopentadienyl and indenyl ligands obtained from lactic acid esters

Lai¹,

Chanon²,

Roussel³

et al. 2008

Journal of Organometallic Chemistry

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“…However, in these cases, the reaction proceeds by successive steps with a base necessary for the deprotonation of cyclopentadienes intermediates [16,17].…”

Section: Resultsmentioning

confidence: 99%

Optically active cyclopentadienyl and indenyl ligands obtained from lactic acid esters

Lai¹,

Chanon²,

Roussel³

et al. 2008

Journal of Organometallic Chemistry

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“…The reactions of unsubstituted cyclopentadiene (5), methylcyclopentadiene (6), and tert-butylcyclopentadiene (7) with phorone (Scheme 2) gave ketones 8, 10, and …”

Section: Resultsmentioning

confidence: 99%

“…The IH NMR spectra of compounds 1, 2, and 7 coincide with those reported previously. [4][5][6] Reaction of 1,3-dimethylcyelopentadiene (1) with phorone.…”

Section: Methodsmentioning

confidence: 99%

Reactions of cyclopentadienes with phorone

Ivchenko

Nifant’ev

et al. 2000

Russ Chem Bull

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Russian Federation. Far: +7 (095) 954 I279Reactions of different cyclopentadienes with phorone were studied, Nonsubstituted and monosubstituted cyclopentadienes form annelation products, viz., 4,4,8,g-tetramethyl-1,3a,4,5.6,7,8.Sa-octa hydroazulen-6-ones.Key words: cyclopentadienes, intermolecular cyclization. Michael addition, azulenones.Recently. I-3 we have studied the reactions of cyclopentadienes and indenes with carbonyl compounds in alkali--aprotic polar solvent systems. It was demonstrated that the two-phase KOH--l.2-dimethoxyethane (DME) mixture is the most efficient system. A wide range of substituted bis(cyclopentadienyl)-and bis(indenyl)methanes were prepared in satisfactory yields with the use of this system. Unexpectedly. z in the reactions of 1,3-dimethylcyclopentadiene (1) and I-methyl-3-phenytcyclopentadiene (2) with acetone, spiro compounds 3 and 4, respectively, rather than the target bis(cyclopentadienyl)methanes were formed as the major products. We suggested that under alkaline conditions, acetone undergoes partial trimerization to form phorone, which reacts with disubstituted cyclopentadienes yielding spiro compounds (Scheme t).To verify this suggestion, we studied the reactions of different cyclopentadienes with phorone under standard conditions (KOH--DME). The results of this investigation are reported in the present work. Results and DiscussionThe reactions of 1,3-dimethyl-and l-methyl-3-phenytcyclopentadiene (1 and 2, respectively) with phorone, like the reactions with acetone, afforded compounds 3 and 4, respectively. The yields of these products were low, 5--10% (t_he..yields were estimated from the analysis of the I H NMR spectra of the reaction mixtures, viz., from the integrated intensities of the characteristic signals for the methylene fragments of compounds 3 and 4).The reactions of unsubstituted cyclopentadiene (5), methylcyclopentadiene (6), and tert-butylcyclopentadiene (7) with phorone (Scheme 2) gave ketones 8, 10, and

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“…KOtBu and elemental grey selenium were obtained from Aldrich and Fluka, respectively. tBu 2 C 5 H 4 [11] was prepared as described previously. Flash chromatography was performed on Merck silica gel (Type 60, 230Ϫ400 mesh ASTM) with petroleum ether as eluent.…”

Section: Methodsmentioning

confidence: 99%