Benzenediazonium‐2‐Carboxylate and Biphenylene

Logullo, Francis M.; Seitz, Arnold H.; Friedman, Lester

doi:10.1002/0471264180.os048.04

Cited by 37 publications

(45 citation statements)

References 11 publications

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“…[21] A 30% yield of biphenylene can be obtained by thermal decomposition of 7 in boiling 1,2-dichloroethane (∼84 • C). [22] The first UV spectrum of gaseous benzyne (λ max = 242 ± 3 nm) was obtained by photolysis of 7. [23] Further details of the UV spectrum of benzyne are reviewed herein.…”

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confidence: 99%

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The Benzyne Story

Wentrup¹

2010

Aust. J. Chem.

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The history of o-benzyne from its early beginnings as an unobservable reactive intermediate until its present status as a very well characterized but still theoretically challenging molecule with important applications in synthesis is reviewed. The m- and p-benzynes, tridehydrobenzenes, and benzdiynes are also known, and p-benzyne is a key intermediate in the action of a potent class of ene-diyne anti-tumour compounds.

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confidence: 99%

“…[26] Compound 7 [22] continues to be an important preparative source of benzyne. [27] Diphenyliodonium carboxylate 8 requires a higher temperature, 160 • C in diglyme, to form benzyne, iodobenzene, and CO 2 .…”

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confidence: 99%

The Benzyne Story

Wentrup¹

2010

Aust. J. Chem.

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“…Synthesis of 9-Triptycylisothiocyanate 3 9-Nitrotriptycene 1 was prepared by the nitration [27] of anthracene followed by the cycloaddition [13] with benzyne generating in situ from benzenediazonium-2-carboxylate [28] according to the literature procedures. The reduction of 1 using SnCl 2 =HCl has been mentioned in the literature [13] but no detailed procedure is given, and we found treatment of 1 with SnCl 2 =HCl in AcOH afforded 9-triptycylamine 2 in 82% yield (Scheme 1).…”

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confidence: 99%

Syntheses of 9-Triptycylisothiocyanate, (10-Amino-9-triptycyl)carboxylic Acid, and Their Derivatives

Xu¹,

Huang²

2014

Synthetic Communications

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In the presence of 1, 8-diazabicyclo[5.4.0]undec-7-ene (DBU), 9-triptycylisothiocyanate has been synthesized in 91% yield from carbon disulfide and sterically hindered 9-triptycylamine at room temperature. 9-Triptycylisothiocyanate can be further converted to 1-benzyl-3-(9-triptycyl)thiourea. (10-Amino-9-triptycyl)carboxylic acid has also been successfully synthesized via a three-step route starting from methyl 10-nitroanthracene-9-carboylate. Its amino and carboxylic groups can undergo acetylation and amidation, respectively.

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“…[23] Furthermore, the derivatives of 1 can be used as spacers and building blocks for functionalized organic materials, [24] together with starting materials for organic synthesis. [25] Many synthetic methods, such as the dimerization of benzyne, [26] the Ullmann coupling of 2,2'-diiodobiphenyl 2 with Cu 2 O or Cu (Scheme 1), [27] pyrolytic extrusion, [28] and the Vollhardt method using cobalt-catalyzed cyclization, [29] have been employed for the preparation of 1 and [n]phenylenes. However, only a few limited methods are known for the construction of functionalized biphenylenes with methyl, fluoro, and other functional groups owing to the difficulty in obtaining the appropriate starting materials.…”

Section: Synthesis Of Biphenylenes and Tetraphenylenesmentioning

confidence: 99%

Copper‐Mediated Aryl‐Aryl Couplings for the Construction of Oligophenylenes and Related Heteroaromatics

Iyoda

2009

Adv Synth Catal

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Efficient methods for the syntheses of biaryls by the copper-mediated homocoupling of arylmetals are summarized. First, a smooth transmetallation between arylzinc halides and copper(II) salts has been employed for the selective homocoupling of arylzinc halides to produce either biphenylenes or tetraphenylenes. This reaction has been applied to the synthesis of cyclic oligothiophenes. Second, an efficient method for the homocoupling of aryl halides by the electron-transfer (ET) oxidation of Lipshutz cuprates [Ar 2 Cu(CN)Li 2 ] with organic electron acceptors has been developed. The ET oxidation of cuprates with 1,4-benzoquinones proceeds smoothly to afford the corresponding coupling products in moderate to high yields. The ET oxidation of cuprates has been applied to the synthesis of either thiophene-or benzene-fused 10-membered ring cyclophanes. For the synthesis of macrocyclic cyclophanes, a linear C À Cu À C structure of Lipshutz cuprates should be maintained in the dimetallacyclic intermediates to efficiently produce large-ring cyclophanes. Moreover, nonaphenylenes and dodecaphenylenes have been synthesized using the ET oxidation of cuprates with duroquinone. Interestingly,

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Benzenediazonium‐2‐Carboxylate and Biphenylene

Abstract: Benzenediazonium‐2‐carboxylate and biphenylene solvent: 50‐ml. portions of 1,2‐dichloroethane product: benzenediazonium‐2‐carboxylate product: biphenylene

Cited by 37 publications

References 11 publications

The Benzyne Story

The Benzyne Story

Syntheses of 9-Triptycylisothiocyanate, (10-Amino-9-triptycyl)carboxylic Acid, and Their Derivatives

Copper‐Mediated Aryl‐Aryl Couplings for the Construction of Oligophenylenes and Related Heteroaromatics

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