Rearrangement of azidoquinones. III. Reaction of 1,4-benzoquinone with sodium azide

Moore, Harold W.; Shelden, H. Raymond; Shellhamer, Dale F.

doi:10.1021/jo01258a115

Cited by 22 publications

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“…Analogous transformations of 1,4-benzo- [11,12] and 1,4-naphthoquinones [11] were also observed in chloroform in an inert atmosphere.…”

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confidence: 64%

“…Couladouros et al [11] proposed a mechanism for the formation of 2-azidonaphthalene-1,4-diol from sodium azide and 1,4-naphthoquinone with participation of acetic acid proton. It was also noted that intramolecular oxidation/reduction of analogous adduct derived from NaN 3 and 1,4-benzoquinone follows a similar scheme, though the reaction was carried out in an aprotic solvent under argon [11,12].…”

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confidence: 97%

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Reaction of N-sulfonyl-1,4-benzoquinone imines with sodium azide

et al. 2016

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Depending on the conditions and the order of addition of the reactants, reactions of N-sulfonyl-1,4benzoquinone imines with sodium azide afforded N-(3-azido-4-hydroxyphenyl)alkane(arene)sulfonamides, N-(3-azido-4-oxocyclohexa-2,5-dienylidene)alkane(arene)sulfonamides, and N-(3,5-diazido-4-hydroxyphenyl)alkanesulfonamides. Quantum chemical calculations showed that the reactions begin with addition of azide ion to the quinone imine.We previously synthesized new N-alkyl(trifluoromethyl)sulfonyl derivatives of 1,4-benzoquinone imine [1] and studied their reactivity toward potassium thiocyanate [1] and sodium arenesulfinates [2]. In the present work we examined reactions of these compounds with sodium azide.

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“…Analogous transformations of 1,4-benzo- [11,12] and 1,4-naphthoquinones [11] were also observed in chloroform in an inert atmosphere.…”

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confidence: 64%

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confidence: 97%

Reaction of N-sulfonyl-1,4-benzoquinone imines with sodium azide

et al. 2016

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“…(1) Preparation of 2,5-diazido-l,4-benzoquinone from sodium azide, acetic acid, and 1,4-benzoquinone [65].…”

Section: Miscellaneous Methodsmentioning

confidence: 99%

Azides

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Organic Chemistry: A Series of Monographs

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“…Both target compounds were synthesized following a two-step protocol ( Fig. 5), previously published for 2,5-diazido-1,4phenylene diacetate by Moore et al (1969). In view of the light sensitivity of the intermediate compound 2,5-diazidobenzene-1,4-diol, all reactions were carried out under light protection.…”

Section: Synthesis and Crystallizationmentioning

confidence: 99%