Dibenzo[a,d]cycloheptene and Related Compounds. III. The Synthesis of Some Analogues of Methadone Containing the Dihydrodibenzo[a,d]cycloheptene and the Tetrahydrodibenzo[a,d]cyclooctene Ring Systems

Horning, D. E.; Muchowski, Joseph M.

doi:10.1139/v71-075

Cited by 6 publications

(1 citation statement)

References 5 publications

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“…Reduction of the nitro groups to the amines and conversion to the phenols was accomplished via a modified Sandmeyer method. 13 The modified method was required, since the diazonium salts containing chloride as the anion are very stable to hydrolysis even upon heating to reflux. 4,4'-Oxydiphenol (28) was synthesized from 4,4'-diaminodiphenyl ether via the same modified Sandmeyer method.…”

Section: Synthesis Of Monomersmentioning

confidence: 99%

Synthesis of high molecular weight poly(ether ketone)s by polycondensation of activated bis(aryl chloride)s with bisphenolates

Percéc

Grigoraş

Clough

et al. 1995

J. Polym. Sci. A Polym. Chem.

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The ability to achieve high molecular weight poly(ether ketone)s from the polycondensation of bis(aryl chloride)s with bis(phenolate)s has been consistently demonstrated. The polymerizations presented here help to delineate for specific bis(aryl chloride)/bisphenolate pairs the reaction conditions required to obtain high molecular weight polymers. Polycondensation of 1,3‐bis(4‐chlorobenzoyl)‐5‐tert‐butylbenzene (6) and 2,2′‐bis(4‐chlorobenzoyl)‐biphenyl (15) with various bisphenolates as well as of 2,2′‐bis(4‐hydroxyphenoxy)biphenyl (33) with 4,4′‐dichlorobenzophenone (41) and 1,3‐bis(4‐chlorobenzoyl)benzene (43) were used as representative model systems to select reaction conditions that led to high molecular weight polymers. © 1995 John Wiley & Sons, Inc.

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Section: Synthesis Of Monomersmentioning

confidence: 99%

Synthesis of high molecular weight poly(ether ketone)s by polycondensation of activated bis(aryl chloride)s with bisphenolates

Percéc

Grigoraş

Clough

et al. 1995

J. Polym. Sci. A Polym. Chem.

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Synthese sieben‐ und fünfgliedriger Ringe aus Allyl‐Kationen

Hoffmann

1973

Angewandte Chemie

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Die Cycloaddition von Allyl-Kationen an konjugierte Diene ist eine wirkungsvolle und allgemein anwendbare Methode zum Aufbau siebengliedriger Carbocyclen. Zur Darstcllung der Allyl-Kationen eignet sich die Silbersalzmethode besonders gut; sie hat selbst in fast aussichtslos scheinenden Fallen Erfolg, z. B. bei den schwierig faBbaren Allyl-Kationen 2-Methylallyl, 2-Methoxyallyl und dem Allyl-Kation selbst. Die Cycloadditionen des 2-Methoxyallyl-Kations erfullen den Prototyp einer 6~,7C-Reaktion in nahezu idealer Weise, da die eingefuhrte Carbonylgruppe einerseits einen Ansatzpunkt fur weitere Umwandlungen bietet, sich abcr andererseits leicht entfernen lafit. Fur die Synthese bietet die Reaktion eines Allyl-Kations rnit x-Reaktanten, vor allem konjugierten Dienen, viele Moglichkeiten. Ein besonderer Vorteil lie@ darin, daB sie es ermoglicht, in einem einzigen Schritt aus einer C3-und einer C4-Einheit ein Gefuge mit bis zu vier ChiralitEtszentren in Form eines Ringes mit mehr als sechs Gliedern aufzubauen. Mit elektronenreichen 2nSystemen bilden die Allyl-Kationen neuartige funfgliedrige Ringe. Dic Natur dcr Organometall-Zwischenstufen konnte in vielen Fallen geklart werden.

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Syntheses of Seven‐ and Five‐Membered Rings from Allyl Cations

Hoffmann

1973

Angew. Chem. Int. Ed. Engl.

190

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The cycloaddition of allyl cations to conjugated dienes offers an efficient and general tool for the construction of seven-membered carbocycles. The silver salt route is highly suitable for generating allyl cations and can be used even in most difficult cases, i. e. for elusive and intractable allyl cations such as 2-methylallyl, 2-methoxyallyl, and the parent allyl cation. Cycloadditions to the 2-methoxyallyl cation come very close to the prototype of a 671,7C reaction, since the carbonyl group introduced into the new ring can either be used for further transformations or be removed altogether. The combination of an allyl cation with K reactants, especially conjugated dienes, is a powerful and strongly convergent synthetic method since it permits one-step assembly, from a C, and a C , unit, of a cluster of up to four chiral centers in a ring which is larger than six-membered. Allyl cations combine with electron-rich 271 systems to form novel five-membered rings. The nature of the organometallic intermediates has been elucidated in many cases.

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Dibenzo[a,d]cycloheptene and Related Compounds. III. The Synthesis of Some Analogues of Methadone Containing the Dihydrodibenzo[a,d]cycloheptene and the Tetrahydrodibenzo[a,d]cyclooctene Ring Systems

Cited by 6 publications

References 5 publications

Synthesis of high molecular weight poly(ether ketone)s by polycondensation of activated bis(aryl chloride)s with bisphenolates

Synthesis of high molecular weight poly(ether ketone)s by polycondensation of activated bis(aryl chloride)s with bisphenolates

Synthese sieben‐ und fünfgliedriger Ringe aus Allyl‐Kationen

Syntheses of Seven‐ and Five‐Membered Rings from Allyl Cations

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