Reactions of trialkyl phosphites with polycyclic p- and o-quinones. Anthraquinone, the pyrenequinones, and the naphthoquinones

Ramírez, Fausto; Bhatia, S. B.; Patwardhan, Anand V.; Chen, Eugene H.; Smith, Clark

doi:10.1021/jo01265a004

Cited by 37 publications

(16 citation statements)

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“…However the reaction of quinones with tertiary phosphanes and phosphites is well reported in the literature and provide to variety of interesting products [19][20][21][22][23][24]. Ramirez et al [19,20,[22][23][24][25] reported the reaction of chloranil with a range of phosphorus compounds including trialkil phosphites, dialkil phosphates and triphenylphosphane to give transient red solutions from which the Fig.…”

Section: Resultsmentioning

confidence: 98%

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Synthesis, spectroscopy and computational studies of some novel phosphorylated derivatives of quinoline-5,8-diones

Nycz

Malecki

Ponikiewski

et al. 2011

Journal of Molecular Structure

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Section: Resultsmentioning

confidence: 98%

“…Ramirez et al [19,20,[22][23][24][25] reported the reaction of chloranil with a range of phosphorus compounds including trialkil phosphites, dialkil phosphates and triphenylphosphane to give transient red solutions from which the Fig. 3.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, spectroscopy and computational studies of some novel phosphorylated derivatives of quinoline-5,8-diones

Nycz

Malecki

Ponikiewski

et al. 2011

Journal of Molecular Structure

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“…[8] Subsequently, Ramirez and co-workers confirmed that the reaction of nitroaryl aldehydes with trialkyl phosphite led to the formation of a (trialkoxy)dioxaphospholane. [9,10] Recently, Liu and Verkade achieved the facile transformation of aryl aldehydes into their respective epoxides by using cyclic aminophosphine, P(MeNCH 2 CH 2 ) 3 N. [11] The efficient preparation of α-hydroxy phosphonates [12] were achieved by the reaction of aryl aldehydes and triethyl phosphite using a Brønsted acid as well as a Lewis acid as catalysts. [13] We have recently reported a ZnBr 2 -mediated Arbuzov reaction to form benzisoxazoles as the sole product.…”

Section: Introductionmentioning

confidence: 99%

Unusual Reactivity of Aryl Aldehydes with Triethyl Phosphite and Zinc Bromide: A Facile Preparation of Epoxides, Benzisoxazoles, and α‐Hydroxy Phosphonate Esters

et al. 2015

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A facile preparation of trans‐epoxides was achieved by a (EtO)3P–ZnBr2‐mediated deoxygenation reaction of the corresponding 2‐nitrobenzaldehydes. The sterically hindered analogues of 2‐nitrobenzaldehyde underwent a reaction with triethyl phosphite in the presence of ZnBr2 as the catalyst to form benzisoxazoles as the sole product. Under identical conditions, the reactions of electron‐rich as well as moderately electron‐deficient aryl aldehydes furnished the corresponding α‐hydroxy phosphonate esters.

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“…Ortho-Quinone Derivatization. Both ortho-and para-quinones are known to form adducts with trimethyl-phosphite [34][35][36]. The reaction of trimethyl phosphite with the ortho-quinone 3,5-di-tert-butyl-l,2-benzoquinone (I) is shown in Figure 3.…”

Section: Trimethyl Phosphite Chemistrymentioning

confidence: 99%

“…Ramierez et al demonstrated that trimethyl phosphite can form an adduct with para-quinones [34,35]. Figure 4 illustrates the reaction of tfimethyl phosphite with the para-quinone 2,6-dimethoxy-l,4-benzoquinone (VI).…”

Section: Para-quinonementioning

confidence: 99%

Investigation of ortho- and para-Quinone Chromophores in Alkaline Extraction Stage Residual Lignins

Zawadzki¹,

Runge²,

Ragauskas³

1999

ACS Symposium Series

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Reactions of trialkyl phosphites with polycyclic p- and o-quinones. Anthraquinone, the pyrenequinones, and the naphthoquinones

Cited by 37 publications

References 0 publications

Synthesis, spectroscopy and computational studies of some novel phosphorylated derivatives of quinoline-5,8-diones

Synthesis, spectroscopy and computational studies of some novel phosphorylated derivatives of quinoline-5,8-diones

Unusual Reactivity of Aryl Aldehydes with Triethyl Phosphite and Zinc Bromide: A Facile Preparation of Epoxides, Benzisoxazoles, and α‐Hydroxy Phosphonate Esters

Investigation of ortho- and para-Quinone Chromophores in Alkaline Extraction Stage Residual Lignins

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