Teraryls via phenylenebis(isobenzofuran) adducts

Leong‐Neumann, S.; Derrick, Sean; Dibble, Peter W.

doi:10.1016/0040-4039(95)00777-a

Cited by 15 publications

(4 citation statements)

References 17 publications

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“…Attempts to form oligomeric rods did not result in extended chain growth, but instead a quadruply bridged cyclophane was formed. Leong-Neumann et al [22] reported the synthesis of teraryls via two novel phenylenebis(isobenzofuran)s but these bis(isobenzofuran)s were too unstable to isolate and were prepared and reacted with dienophiles in situ. Yu et al [23] reported the synthesis of naphtho[1,2-c;3,4-c]difuran which could be isolated and characterized.…”

Section: K a Watson And R G Bassmentioning

confidence: 99%

Polymer Synthesis via a Diels–Alder Reaction between Bis(Isobenzofuran)s and Bis(Phenylacetylene)s Containing Preformed Phthalimide Rings

Watson

Bass

2000

High Performance Polymers

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Polymers have been prepared by the Diels-Alder reaction between novel bis(isobenzofuran)s and bis(phenylacetylene)s containing preformed phthalimide rings. The initial polymer undergoes a thermal rearrangement without volatile evolution that effectively prevents a retro Diels-Alder reaction from occurring. The polymers were soluble in common organic solvents such as chloroform, N-methyl-2-pyrrolidinone, N,N-dimethylacetamide and chlorinated aromatic solvents. The polymers exhibited glass transitions ranging from 251 to 359 • C and a 10% weight loss ranging from 451 to 486 • C in air and 482 to 520 • C in helium as determined by thermogravimetric analysis. This synthetic approach offers advantages over other Diels-Alder polymerizations since no volatile by-products are generated and a thermal rearrangement eliminates a retro Diels-Alder reaction.

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Section: K a Watson And R G Bassmentioning

confidence: 99%

Polymer Synthesis via a Diels–Alder Reaction between Bis(Isobenzofuran)s and Bis(Phenylacetylene)s Containing Preformed Phthalimide Rings

Watson

Bass

2000

High Performance Polymers

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“…Isobenzofuran (IBF) ( 1 , Figure ) is a fundamentally interesting molecule that has seen significant use in chemical synthesis − and has been of substantial theoretical interest. − IBFs undergo rapid Diels−Alder cycloaddition with a variety of dienophiles and have found use in a variety of fields from natural product synthesis and polycyclic aromatic hydrocarbons to the formation of open fullerenes. − There has also been interest in the relative reactivity of IBF and its benzologues such as naphtho[1,2- c ]furan 2 . Recently we have become interested in the synthesis and use of bis(isobenzofuran)s, two reactive IBF entities coupled together, as linker molecules , and as cyclophane precursors. We have reported the synthesis of naphtho[1,2- c :5,6- c ]difuran, 3a , and described its use as a cyclophane precursor .…”

Section: Introductionmentioning

confidence: 99%

“…[12][13][14] There has also been interest in the relative reactivity of IBF and its benzologues such as naphtho[1,2-c]furan 2. 15 Recently we have become interested in the synthesis and use of bis(isobenzofuran)s, two reactive IBF entities coupled together, as linker molecules 16,17 and as cyclophane precursors. We have reported the synthesis of naphtho[1,2-c:5,6-c]difuran, 3a, and described its use as a cyclophane precursor.…”

Section: Introductionmentioning

confidence: 99%

X-ray Structures of Cyclophanes Derived from Naphtho[1,2-c:5,6-c]difuran and the Synthesis, Structure, and Reaction Kinetics of Its 1,3,6,8-Tetrasilylated Derivative

et al. 2009

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A silylated derivative of naphtho[1,2-c:5,6-c]difuran, 1,3,6,8-tetrakis(tert-butyldimethylsilyl)naphtho[1,2-c:5,6-c]difuran, has been isolated and its X-ray crystal structure determined. Bond localization confirms the polyene character of this isobenzofuran ring system. This molecule undergoes two successive Diels-Alder reactions with second-order rate constants differing by over 2 orders of magnitude, consistent with predictions based on their structure-count ratios and with the reactivity of the novel 1,3-bis(tert-butyldimethylsilyl)isobenzofuran. Crystal structures of two cyclophanes derived from the reaction of naphtho[1,2-c:5,6-c]difuran and bis(imide) or bis(ester) dienophiles show marked differences in the conformation of the aliphatic chain found in the solid state.

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“…Although the azasilacyclopentadiene moiety did not participate in this transformation, the cooperation between the azasilacycle and the zirconacycle resulted in unprecedented cyclization chemistry upon hydrolysis. Hydrolysis of 6 afforded the butadiene-fused aminotetrahydrofuran derivatives 7 , which are useful but not accessible by other means . The single-crystal structure of 7b and a proposed mechanism for the hydrolysis process of 6 are given in the Supporting Information.…”

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confidence: 99%

Cleavage and Reorganization of Zr−C/Si−C Bonds Leading to Zr/Si−N Organometallic and Heterocyclic Compounds

Zhang

Zhao

et al. 2010

J. Am. Chem. Soc.

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The t-BuCN-stabilized zirconacyclopropene-azasilacyclopentadiene complexes 2 are generated in situ in high yields from the Si-tethered diynes, Cp(2)Zr(II) species, and 2 equiv of t-BuCN via a coordination-induced Zr-C/Si-C bond cleavage and reorganization. Complexes 2 have been demonstrated to be synthetically very useful. A variety of novel Zr/Si organo-bimetallic compounds and Si/N heterocyclic compounds, such as azasilacyclopentadienes, azasilacyclohexadienes, and allenylazazirconacycles, are obtained in high yields when complexes 2 are treated with ketones, carbodiimides, alkynes, elemental sulfur (S(8)), acid chlorides, or nitriles. In this chemistry, t-BuCN behaves as both an initiator and a brake/release handle to initiate and control the reaction process.

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Teraryls via phenylenebis(isobenzofuran) adducts

Cited by 15 publications

References 17 publications

Polymer Synthesis via a Diels–Alder Reaction between Bis(Isobenzofuran)s and Bis(Phenylacetylene)s Containing Preformed Phthalimide Rings

Polymer Synthesis via a Diels–Alder Reaction between Bis(Isobenzofuran)s and Bis(Phenylacetylene)s Containing Preformed Phthalimide Rings

X-ray Structures of Cyclophanes Derived from Naphtho[1,2-c:5,6-c]difuran and the Synthesis, Structure, and Reaction Kinetics of Its 1,3,6,8-Tetrasilylated Derivative

Cleavage and Reorganization of Zr−C/Si−C Bonds Leading to Zr/Si−N Organometallic and Heterocyclic Compounds

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