Über eine synthetische Bildungsweise des Pyrens

Freund, Martin; Fleischer, Karl

doi:10.1002/jlac.19144020104

Cited by 8 publications

(3 citation statements)

References 2 publications

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“…Using these reaction conditions [4-(1-pyrenyl)butyl] 3,4,5-tris(12,12,12, 11,11,10,10,9,9,8,8,7,7,6,6,5,5-heptadecafluoron-dodecan-1-yloxy)benzoate (35) was achieved in 60% yield.…”

Section: Chemical Reviewsmentioning

confidence: 98%

“…This pyrene monomer 41 was used to prepare the poly(pyridine-imide) for optoelectric applications. As will be 11,11,10,10,9,9,8,8,7,7,6,6,5,5-heptadecafluoro-n-dodecan-1-yloxy)benzoate (35). described, the optical properties of this polymer can be modulated upon protonation of the pyridine unit.…”

Section: Chemical Reviewsmentioning

confidence: 99%

“…The search for an effective method to prepare pyrene lead Weitzenböck in 1913 to the first synthesis of pyrene, starting from o , o ′-ditolyl . Until the 1950s, several other preparative routes toward pyrene were presented. − Modernization of the distillation process of coal tar, as well as the destructive hydrogenation of hard coal, yielded considerable quantities of pyrene and other polycyclic hydrocarbons, making pyrene of commercial use.…”

Section: Introductionmentioning

confidence: 99%

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Pyrene-Based Materials for Organic Electronics

2011

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“…Using these reaction conditions [4-(1-pyrenyl)butyl] 3,4,5-tris(12,12,12, 11,11,10,10,9,9,8,8,7,7,6,6,5,5-heptadecafluoron-dodecan-1-yloxy)benzoate (35) was achieved in 60% yield.…”

Section: Chemical Reviewsmentioning

confidence: 98%

Section: Chemical Reviewsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Pyrene-Based Materials for Organic Electronics

2011

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Synthesis and Valence Isomerization of 2, 7-Dihydro-2, 2, 7, 7-tetramethylpyrene

Ackermann

Angliker

Hasler

et al. 1982

Angew. Chem. Int. Ed. Engl.

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Synthesis and Valence Isomerization of 2 , ? -D i h y d r 0 -2 , 2 , 1 , 7 -t e t r a m 1The potential to study the photochemical and thermal valence isomerization shown in Scheme 1 has been our prime incentive to synthesize the cross-conjugated polyene 2.7-dlhydropyrene. We have chosen the blocked and sterically shielded derivative 2,7-dihydro-2,2,7,7-tetramethylpyrene (1) as a model compound to protect the system against polymerization, tautomerization, disproportionation, and oxidation/l/. Briv.-l)oz. Dr. J. Wirz, Dip1.-Chem. E. Hasler, Dr. H. Angliker, Dip1.-Chem. J. Ackermann, Physikalisch-Chemisches Institut der Wniversitat Basel, Klingelbergatrasse 80, CH-4056 Basel (Switzerland). ** This work is part of project nr. 2.616-0.80 of the Swiss National Science Foundation. Due to the geometrical constraints, the ring opening of a cyclopropane fused to the peri-positions of naphthalene can proceed only in a disrotatory manner; the valence isomerizations (L)* (2,syn) and (?,anti) therefore classify as intramolecular n 6 s + n6s and rr6a + s i o n s , respectively. They are thus "forbidden" in the sense of the Woodward-Hoffmann rules /2/ and are likely to proceed via a reactive biradlcal intermediate (2) with the n-topology Of 1,8-naphthoquinodimethane / 3 / . cycloadditions/rever--Scheme 1: ( 1 ) (3) -1430 -(2,syn) (2,ontilThe preparation of (1) was achieved in five steps starting from naphthalene-l,4,5,8rtetracarboxylic acid dianhydride ( : I by the reaction sequence shown in scheme 2 (preparative procedures are given below). To date, we have obtained the tetraketone ( 2 ) in poor yields only (5% relative to (q)), whereas the three-step reduction of (2) to (1) proceeded smoothly (overall yields > 50%) without isomer separation of the intermediate products (0, RIOH and Br, resp.). The dihydropyrene (1) is isolable as a yellow, crystalline solid (dec. 180°1 and is stable in aerated solutions when light is rigorously excluded. The NMR chemical shifts of the vinyl hydrogens substantiate the expected polyene character of and provide no evidence for the presence of an 'aromatic" ring current in the central naphthalene moiety.

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Über Malonylbromid und eine Synthese des peri ‐Acenaphth‐indandions

Fleischer¹,

Hittel²,

Wolff³

1920

Ber. dtsch. Chem. Ges. A/B

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0 -[ 3, $-D i c h l o r -i -p r o p y 1 Jrno r p h i n. D a im I3enzolsulfosaure-[B,P'-dichlor i-propyll-ester die Sulfosaureester-Bindung infolge der sterischen Hinderung der benachbarten bei-&n ChlOrntOme ungemein schwer verseifbar iot, war von einem Versiich zur Darstellung von reinem [ Dichlor-i-propy1Jmorphin mittels dieses Esters nicht vie1 z u hoffen. Die diesbezuglichen Yersucbe blieben dann auch im wesentlichen erfolglos. Das erhaltene [Dichlor-I prnpyll-morphin-Chlorh~drat vorn Schmp. 147' erwies sich trotz .tlreimnligem Umkrystallisieren und konstnntem Schmp. als unrein. Auch die freie B a s e vorn Schmelzpunkt 1 1 5 O war nicht rein zu rrbalten.

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Über eine synthetische Bildungsweise des Pyrens

Cited by 8 publications

References 2 publications

Pyrene-Based Materials for Organic Electronics

Pyrene-Based Materials for Organic Electronics

Synthesis and Valence Isomerization of 2, 7-Dihydro-2, 2, 7, 7-tetramethylpyrene

Über Malonylbromid und eine Synthese des peri ‐Acenaphth‐indandions

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