- Synthesis and characterization of aromatic poly(amides) based on 3,5-diamino-N-cyclopropylbenzamide
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Three aromatic poly(amides) (PAs) were prepared, one of them containing a dimethyldiphenylsilane unit from a new aromatic diamine monomer with a bulky pendant polar group. All PAs were obtained in high yield and the inherent viscosities were in the range
- Tundidor-Camba,Terraza,Tagle,Coll,Ojeda,Pino
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p. 23057 - 23066
(2015/03/14)
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- Synthesis of heterocyclic monomers via Reissert chemistry
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The chemistry of Reissert compounds has been used to synthesize activated difluorotetraketone monomers containing two coupled isoquinolyl moieties, linked at either the 1,1'-or 4,4'-positions. These monomers offer routes to novel families of poly(heteroarylene ether)s. New 4,4'-coupled bis(Reissert compound) 9 containing 4,4'-diketo moieties failed to afford the desired difluorotetraketo monomer upon attempted rearrangement. However, analogous bis(Reissert compound) 19 containing 4,4'-dibenzyl units did so, via aldehyde condensation, hydrolysis of the intermediate ester and oxidation of the four benzylic moieties to keto groups; thus the novel difluorotetraketone monomer 10 was prepared. Novel bis(Reissert compound)s 24, 28, and 35 were synthesized from diacid chlorides and 4-(pfluorobenzyl)isoquinoline. Rearrangement of 24 to the diketone 29, followed by oxidation of the 4-benzyl moieties resulted in difluorotetraketone monomer 30 containing a 1,1'-linked bisisoquinoline. The 1,1'-linked bis(isoquinolylfluorodiketo) monomer 38, isomeric with 10, was prepared from 4-(p-fluorobenzyl) Reissert compound 36 by condensation with terephthaldehyde, ester hydrolysis to diol 37, and oxidation. In the course of this effort, a number of new isoquinoline Reissert compounds were synthesized as model systems.
- Gibson, Harry W.,Brumfield, Kimberly K.,Grisle, Roger A.,Hermann, Christine K. F.
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p. 3856 - 3867
(2011/11/13)
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- KINETICS AND MECHANISM OF THE REACTION OF CARBOXYLIC ACIDS WITH THIONYL CHLORIDE IN THE PRESENCE OF DIMETHYLFORMAMIDE
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A study was carried out on the reaction of carboxylic acids with thionyl chloride in the presence of dimethylformamide.Correlation analysis of a reaction series of substituted benzoic acids with thionyl chloride indicated that this reaction is electrophilic in nature.The ionic complex of dimethylformamide and thionyl chloride reacts rapidly with the carboxylic acid to release hydrogen chloride and form the chloride of the mixed anhydride of thiodimethyliminium and the carboxylic acid, which undergoes rearrangement in the rate-limiting step to regenerate the catalyst and liberate the acid chloride and sulfur dioxide.
- Vulakh, E. L.,Ivanova, V. M.,Nemleva, S. A.
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p. 620 - 627
(2007/10/02)
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