The Reaction between Quinones and Metallic Enolates. XIX.<sup>1</sup> The Structure of Diduroquinone

Smith, Lee Irvin; Tess, Roy W.; Ullyot, Glenn E.

doi:10.1021/ja01236a035

Cited by 20 publications

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“…11 (yellow solid, 38 mg, 38%). Proton NMR spectra of the purified product from both reactions are consistent with that of the recrystallized product synthesized by literature procedures . Mp: 187–189 °C.…”

Section: Methodssupporting

confidence: 62%

“…The more sterically hindered duroquinone, 2i, does not react as an electrophile with the NHCs 1a and 1b. Instead, the NHCs act as Brønsted bases to initiate the dimerization of 2i into the previously reported diduroquinone (11) 72 in moderate yields (with 1a, 45%; with 1b, 38%; Scheme 7). By contrast, no reaction was observed between NHC 1a or 1b and Kharasch's 3,3′,5,5′-tetra-tert-butyldiphenoquinone (2j), which lacks acidic protons.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…13 the purified product from both reactions are consistent with that of the recrystallized product synthesized by literature procedures. 72 Reactions of NHCs with Diphenoquinones. With 2j.…”

Section: ■ Conclusionmentioning

confidence: 99%

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Addition, Substitution, and Ring-Contraction Reactions of Quinones with N-Heterocyclic Carbenes

et al. 2018

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Despite the common use of quinones as oxidizing agents in N-heterocyclic carbene (NHC)-based organocatalysis and transition-metal catalysis, the direct reactivity of quinones with NHCs remains underexplored. In this paper, we report the reactivity of NHCs with common p- and o-quinones, uncovering three unreported reactions involving contractions of the quinone ring that lead to push-pull furanolactone chromophores, NHC fulvalenes, and α-acylimidazolium cyclopentenone derivatives. These experiments also provide a rationale for the superior compatibility of tetra- tert-alkylated diphenoquinones in NHC-based oxidative transformations.

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Section: Methodssupporting

confidence: 62%

Section: ■ Results and Discussionmentioning

confidence: 99%

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Addition, Substitution, and Ring-Contraction Reactions of Quinones with N-Heterocyclic Carbenes

et al. 2018

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Stereoselective hetero-Diels-Alder reactions: structure determination of new xanthenedione derivatives by NMR spectroscopy and x-ray crystallography

1999

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TheMichael Reaction*This cooperative study was begun when the three authors were working at the Weizmann Institute of Science, Rehovoth.

Bergmann¹,

Ginsburg

Pappo

2011

Organic Reactions

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The Michael condensation in its original scope is the addition of an addend or donor containing an alpha‐hydrogen atom in the system OCCH to a carbon‐carbon double bond that forms part of a conjugated system of the general formula CCCO in an acceptor. The condensation takes place under the influence of alkaline reagents, typically alkali metal alkoxides. The range of addends is very broad. Typical acceptors are alpha, beta‐unsaturated aldehydes, keotnes, and acid derivatives. As an extension of the original scope, the Michael condensation has come to be understood to include addends and acceptors activated by groups other than carbonyl and carboxalkoxy. The wider scope is encompassed in this survey.

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The Reaction between Quinones and Metallic Enolates. XIX.¹ The Structure of Diduroquinone

Cited by 20 publications

References 0 publications

Addition, Substitution, and Ring-Contraction Reactions of Quinones with N-Heterocyclic Carbenes

Addition, Substitution, and Ring-Contraction Reactions of Quinones with N-Heterocyclic Carbenes

Stereoselective hetero-Diels-Alder reactions: structure determination of new xanthenedione derivatives by NMR spectroscopy and x-ray crystallography

TheMichael Reaction*This cooperative study was begun when the three authors were working at the Weizmann Institute of Science, Rehovoth.

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The Reaction between Quinones and Metallic Enolates. XIX.1 The Structure of Diduroquinone

Cited by 20 publications

References 0 publications

Addition, Substitution, and Ring-Contraction Reactions of Quinones with N-Heterocyclic Carbenes

Addition, Substitution, and Ring-Contraction Reactions of Quinones with N-Heterocyclic Carbenes

Stereoselective hetero-Diels-Alder reactions: structure determination of new xanthenedione derivatives by NMR spectroscopy and x-ray crystallography

TheMichael Reaction*This cooperative study was begun when the three authors were working at the Weizmann Institute of Science, Rehovoth.

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The Reaction between Quinones and Metallic Enolates. XIX.¹ The Structure of Diduroquinone