Zur Kenntnis des Dinaphtylen‐dioxyds. II

Pummerer, Rudolf; Rieche, Alfred; Krüdener, Georg v.; Pfeiffer, Hans H.; Prell, Ernst; Tuchmann, Walter; Wilsing, Heinrich

doi:10.1002/jlac.19335030103

Cited by 4 publications

(3 citation statements)

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“…In particular, the chiral analogue 98.5 , described in 1966 by Blackburn, Cameron, and Chan, was obtained by dimerization of the quinone precursor 98.3 , followed by acetylation of the intermediate “xylaphin” 98.4 . The unsubstituted chromophore, xantheno[2,1,9,8- klmna ]xanthene-4,10-dione 98.8 , was synthesized earlier by Pummerer and co-workers by means of Cu-mediated cyclization of 1,1′-bi-2-naphthol 98.6 , followed by oxidation with peroxymonosulfuric acid . The intermediate “dinaphthylene dioxide” 98.7 , also known as dioxaanthranthrene or peri -xanthenoxanthene (PXX), , is an interesting fused system in itself, and a range of its extended analogues such as 98.11 , 98.12 , or 98.13 were subsequently prepared.…”

Section: Pyrenoidsmentioning

confidence: 99%

“… a Reagents and conditions: (a) naphthalene-2,3-diol, phosphate buffer of pH 6.6, N 2 atm, 12 h, rt; (b) CH 3 COONa, (CH 3 CO) 2 O, Zn dust, 2 h, reflux; (c) (CH 3 COO) 2 Cu, 8% caustic soda, H 2 O, 2 h, 280–290 °C; (d) (1) H 2 SO 4 , H 2 SO 5 , ice, H 2 O, 24 h, rt, (2) H 2 SO 4 , ice, 24 h, rt, (3) H 2 SO 4 , H 2 O; (e) TFA, VOF 3 , 15 h, rt. …”

Section: Pyrenoidsmentioning

confidence: 99%

“…515 The unsubstituted chromophore, xantheno[2,1,9,8-klmna]xanthene-4,10-dione 98.8, was synthesized earlier by Pummerer and co-workers by means of Cu-mediated cyclization of 1,1′-bi-2-naphthol 98.6, 516 followed by oxidation with peroxymonosulfuric acid. 517 The intermediate "dinaphthylene dioxide" 98.7, also known as dioxaanthranthrene or peri-xanthenoxanthene (PXX), 518,519 is an interesting fused system in itself, and a range of its extended analogues such as 98.11, 520 98.12, 521 or 98.13 522 were subsequently prepared. The xylindein chromophore was also obtained in an unexpected rearrangement of the dinaphthofuran 98.9, which Scheme 95.…”

Section: Oxa-and Thiapyrenoidsmentioning

confidence: 99%

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Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

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Two-dimensionally extended, polycyclic heteroaromatic molecules (heterocyclic nanographenes) are a highly versatile class of organic materials, applicable as functional chromophores and organic semiconductors. In this Review, we discuss the rich chemistry of large heteroaromatics, focusing on their synthesis, electronic properties, and applications in materials science. This Review summarizes the historical development and current state of the art in this rapidly expanding field of research, which has become one of the key exploration areas of modern heterocyclic chemistry.

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Section: Pyrenoidsmentioning

confidence: 99%

Section: Pyrenoidsmentioning

confidence: 99%

Section: Oxa-and Thiapyrenoidsmentioning

confidence: 99%

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Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

et al. 2016

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Über Dinaphthylendiimin und Dehydrodinaphthylendiimin

Rieche¹,

Rudolph²,

Seifert³

1940

Ber. dtsch. Chem. Ges. A/B

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Zur Kenntnis des Dinaphtylendioxyds. III. Mitteilung. Acylierung und Nitrierung

Pummerer¹,

Buchta²,

Gündel³

et al. 1942

Justus Liebigs Ann. Chem.

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A. I. Die Boylierung des Dinaphtylendioxyds und der Aufbau h6herer11. Diphtaloylsiiure des Dinaphtylendioxydw und RingsohluB zum Ringsysteme. Diphtaloyldinaphtylendioxyd. B.Nitrierung des Dinaphtylendioxyds. I. Die Mononitroverbindungen und Monamine. II. DieDinitro-und Diaminoverbindungen. Vereuohe zu A und B. Anhang. Nitrierung von 4,4'-Dinepht~ndioxyd. Bearbeitet von A. Rieche u. P. v. M i l k .Nachdem in der I. Xtteilung das Ringsystem des Dinaphtylendioxyds durch die Kupferosyd-Nitrobenzolschmelze des B-Dinaphtols leicht zuganglich gemacht war, murden in der 11. Mitteilung verschiedene Oxydationsmittel auf ihr Verhalten gegen das Dioxyd studiert und gezeigt, daS sie unter Bildung eines Chinons in 4-und 4'-Stellung angreifen, so da13 man zum 4,4'-Dinaphtondioxyd kommt, dessen Konstitution durch eine einwandfreie Synthese ausgehend vom 4-Amino-2-naphtol bewiesen 'werden konnte. Von der Technik ist ja iiberhaupt die Synthese substituierter Dioxyde aus definierten ,B-Naphtol-. derivaten bevorzugt morden, wie Rich aus dem Studium I) I. Mittdusg, 13.59,2169 (1926); II. Mitteilung, A. 608,40 (1933). Annalen der Chemie. 668. Band. 8 2. Der A 7 1 f baic liiiherer R iugs ys t enie a . 2~ o-Bro nbmtzo y ldwi.uaten des L)i~~aphtUleizdiozUds (S t inzend6rf er). Mit o-RPo~benzoylclilo~id eritst.chen wie bei dem nicht, bromicrten SBurechlorid cin Mono-und ein Di-o-brombenzoylderivat. ncbeneinander. In beiden FBllen 1Sl3t sich durch I ) Erlnngen, 1936 : Cber Mono-und Dibenzoyien-dinaphtylendioxyd. 2, Ubcr Kondensationen von Phtalsiiureenhydrid und Binaphtylcndioxyd. Disu. Erlangen 1927; vgl. A. 11. I ) B. 68, 800, 2222 (1936). 1) Vgl. Anm. 2, 6. 106. 2, a. a. 0.

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Zur Kenntnis des Dinaphtylen‐dioxyds. II

Cited by 4 publications

References 5 publications

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

Über Dinaphthylendiimin und Dehydrodinaphthylendiimin

Zur Kenntnis des Dinaphtylendioxyds. III. Mitteilung. Acylierung und Nitrierung

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