2H-Dibenz[c,d,h]azulen-2-one

Galantay, Eugene; Agahigian, Harry; Paolella, Nicholas

doi:10.1021/ja00968a047

Cited by 6 publications

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“…1 H, 13 C and 19 F NMR spectra were recorded on Varian 300, 400, 500 or 600 MHz spectrometers. Assignments were based on standard 2-dimensional NMR techniques ( 1 H-1 H COSY, 1 H- 13 C HSQC and HMBC, NOESY).…”

Section: Methodsmentioning

confidence: 99%

“…Moreover, it was suggested that the favoured resonance structure would be zwitterionic whereby the ring system behaved as a dibenz[cd,h]azulenium cation. 19 More recently, a series of 7H-naphth[3,2,1-cd]azulene-7-ones have been prepared. 20 In the light of these observations, it was thought that the reaction of bromo-allene 20a with an acid followed by hydride addition, would bring about formation of a phenyl-substituted dibenz[cd,h]azulene.…”

Section: Synthesis Of 2-phenyl-11bh-dibenz[cdh]azulenementioning

confidence: 99%

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Syntheses, X-ray crystal structures and reactivity of fluorenylidene- and dibenzosuberenylidene-allenes: convenient precursors to dispirotetracenes, di-indenotetracenes and 2-phenyl-11bH-dibenz[cd,h]azulene

et al. 2010

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3,3-(Biphenyl-2,2'-diyl)-1-alpha,alpha,alpha-trifluoro-p-tolyl-allene, 9, sequentially forms head-to-tail, 12, cis-tail-to-tail, 13, and trans tail-to-tail, 14, 1,2-dialkylidene-cyclobutane dimers, each of which has been characterised by X-ray crystallography. Thermolysis at 180 degrees C yields the dispirotetracene, 15, and di-indenotetracene, 16; the latter compound forms an air-stable Diels-Alder adduct, 17, with N-methylmaleimide. In contrast, the dibenzo[a,d]cycloheptenylidene-allenes, (C(14)H(10))C=C=C(Br)Ph, 20a, and (C(14)H(10))C=C=C(H)Ph, 21a, do not dimerise under relatively mild conditions. However, protonation of the bromo-allene, 20a, and subsequent addition of hydride, provide a facile entry to the difficultly accessible bowl-shaped dibenz[cd,h]azulene framework, as in 30, that had not previously been structurally characterised. Among others, the X-ray crystal structures of 12, 13, 14, 17, 20a, 21a and 30 are reported.

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Section: Methodsmentioning

confidence: 99%

Section: Synthesis Of 2-phenyl-11bh-dibenz[cdh]azulenementioning

confidence: 99%

Syntheses, X-ray crystal structures and reactivity of fluorenylidene- and dibenzosuberenylidene-allenes: convenient precursors to dispirotetracenes, di-indenotetracenes and 2-phenyl-11bH-dibenz[cd,h]azulene

et al. 2010

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Cycl[4.3.2]azin‐4,5‐dicarbonsäure‐diäthylester

Flitsch

Müter

1973

Angewandte Chemie

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Diethyl Cycl[4.3.2]azine‐4,5‐dicarboxylate

Flitsch

Müter

1973

Angew. Chem. Int. Ed. Engl.

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Retention of the silicon-silicon bonds in all the carbene reactions described above was demonstrated, not only by analytical and spectral data of the isolated products, but also by spontaneous evolution of hydrogen on alkaline hydrolysis and reduction of Ag' ions to metallic silver. (2): Phenyl(trichloromethyl)mercury (1 5 g, 38 mmol) was heated with hexachlorodisilane ( I ) (21 g, 77 mmol) and NaI (0.5 g) under argon for 6 h at 120 "C (bath temperature). The solid that separated was filtered off after addition of light petroleum. Fractional distillation of the filtrate gave pure ( 2 ) , b. p. 68 "CIO.6 torr (32 YO yield, 4.2 g), along with ( I ), b. p. 25"C/3 torr. The product (2) (4.0g) was also obtained analogously from (bromodichloromethy1)phenylmercury ( I 5 g) and ( I ) (21 g). IR (capillary; cm-I): 860s, 790m, 732vs, 702s, 610vs, 590vs, 580vs, 525s, 498s, 458s, 448m, 420s, 360s, and 342 m. Pentachloro( trich1oromethyl)disiiane

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2H-Dibenz[c,d,h]azulen-2-one

Cited by 6 publications

References 0 publications

Syntheses, X-ray crystal structures and reactivity of fluorenylidene- and dibenzosuberenylidene-allenes: convenient precursors to dispirotetracenes, di-indenotetracenes and 2-phenyl-11bH-dibenz[cd,h]azulene

Syntheses, X-ray crystal structures and reactivity of fluorenylidene- and dibenzosuberenylidene-allenes: convenient precursors to dispirotetracenes, di-indenotetracenes and 2-phenyl-11bH-dibenz[cd,h]azulene

Cycl[4.3.2]azin‐4,5‐dicarbonsäure‐diäthylester

Diethyl Cycl[4.3.2]azine‐4,5‐dicarboxylate

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