Carbonyl Bridge Compounds and Related Substances.

Allen, C. F. H.

doi:10.1021/cr60117a002

Cited by 46 publications

(15 citation statements)

References 67 publications

(146 reference statements)

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“…In 1968, Bryce-Smith and Gilbert reported the photolytic decarbonylation of -diketone 15 to form tetrachloro-o-terphenyl 21 both in solution and in the crystalline state under visible light (Scheme 1) [48]. While the thermal decarbonylation of monoketone compounds was already well-documented by then [49], the photoinduced decarbonylation of -diketones had been unknown until this report. Almost at the same time, Strating and coworkers reported that -diketones 16-19 underwent smooth photolysis to form the corresponding aromatic compounds (Scheme 1) [50].…”

Section: Synthesis and Photoreactivity Of -Diketone-type Precursors mentioning

confidence: 93%

Synthesis and photoreactivity of α-diketone-type precursors of acenes and their use in organic-device fabrication

Suzuki

Aotake

Yamaguchi

et al. 2014

Journal of Photochemistry and Photobiology C: Photochemistry Re

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Acenes are highly promising p-type organic semiconductors, and have been the subject of intense studies. However, acenes are often low in solubility and stability, which poses major obstacles in the synthesis and processing of this class of compounds. In order to overcome the problem, a series of diketone-type acene precursors have been developed. These precursors are generally more soluble and stable than the corresponding acene compounds, and their quantitative conversion can be achieved simply by photoirradiation both in solution and in the solid state. Further, the irreversible photoinduced removal of the -diketone unit can be used to alter the optoelectronic properties of fluorophores. This review overviews the synthesis and photochemical properties of -diketone-type acene precursors, as well as their use as intermediates in preparation of large acenes or highly functionalized acene derivatives. Computational studies on the mechanism of -diketone photolysis and the use of diketone derivatives in fabrication of organic devices are also summarized in this review.

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Section: Synthesis and Photoreactivity Of -Diketone-type Precursors mentioning

confidence: 93%

Synthesis and photoreactivity of α-diketone-type precursors of acenes and their use in organic-device fabrication

Suzuki

Aotake

Yamaguchi

et al. 2014

Journal of Photochemistry and Photobiology C: Photochemistry Re

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“…Addition reactions of tetraphenylcyclopentadienone, often abbreviated to 'tetracyclone', were reviewed by Allen (1945Allen ( , 1962. Tetracyclone reacts with unsaturated anhydrides, acids and esters, forming a number of polyfunctional carbonylbridge compounds.…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure of dimethyl 3,4,5,6-tetraphenylcyclohexa-3,5-diene-1,2-dicarboxylate

Greenberg

Nazarenko

2016

Acta Cryst E

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“…The adducts usually possess a six-membered carbocyclic ring containing one or two double bonds and may have in addition a 1,4-bridge consisting of one or two carbon atoms or a heteroatom. Aromatization is induced by dehydrogenation (2), dehydrohalogenation (3), deamination (4), pyrolytic elimination of substituents (5), or a 1,4-bridge (6), or fission of a 1,4-oxygen bridge followed by loss of H,O (7). Less general procedures for the annelation of readily available molecules to benzene rings include the catalytic trimerization of acetylenes (8), the reaction of pyrylium salts with nitromethane (9), or triphenylphosphinemethylene (lo), the condensation of pyrones with Grignard reagents (1 l), the ketovinylation of P-dicarbonyl compounds followed by intramolecular cyclization or further reaction with P-chlorovinyl ketones (12), and the reaction of enamines with esters of acetylenedicarboxylic acid (13).…”

Section: Introductionmentioning

confidence: 99%

Influence of Lewis acids on the Diels–Alder reaction. II. Rearrangement of 1- and 1,4-substituted diethyl 7-oxabicyclo[2•2•1]2,5-heptadiene-2,3-dicarboxylate adducts to 4- and 4,6-substituted diethyl 3-hydroxyphthalates

Mcculloch¹,

Stanovnik²,

Smith³

et al. 1969

Can. J. Chem.

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Direct formation of 4-or 4,6-alkyl and aryl substituted diethyl 3-hydroxyphthalates from the correspondingly substituted Diels-Alder adducts of 2-or 2,5-substituted fi~rans and diethyl acetylenedicarboxylate is pronloted by AICI, in CH2C12 at room temperature. The first adduct of 2,5-diphenylfuran to be isolated has been obtained from the same reaction at -20'. The aromatic compounds can be obtained alternatively by treating the adducts with BF, or H2S04: where the adducts can be prepared by conventional means this two-step procedure has resulted in greatly improved yields. Adducts of furan and furfuryl alcohol are similarly converted to substituted phenols. HCI effected conversion only in the case of adducts carrying a bridgehead aryl substituent; in all other cases HCI added to the substituted double bond. The mechanism of the adduct rearrangement is discussed.

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Carbonyl Bridge Compounds and Related Substances.

Cited by 46 publications

References 67 publications

Synthesis and photoreactivity of α-diketone-type precursors of acenes and their use in organic-device fabrication

Synthesis and photoreactivity of α-diketone-type precursors of acenes and their use in organic-device fabrication

Crystal structure of dimethyl 3,4,5,6-tetraphenylcyclohexa-3,5-diene-1,2-dicarboxylate

Influence of Lewis acids on the Diels–Alder reaction. II. Rearrangement of 1- and 1,4-substituted diethyl 7-oxabicyclo[2•2•1]2,5-heptadiene-2,3-dicarboxylate adducts to 4- and 4,6-substituted diethyl 3-hydroxyphthalates

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