Construction of polyaromatics via photocyclization of 2-(fur-3-yl)ethenylarenes, using a 3-furyl group as an isopropenyl equivalent synthon

Chen, Ying-Zhe; Ni, Ching-Wen; Teng, Fu‐Lin; Ding, Yi-Shun; Lee, Tunng-Hsien; Ho, Jau Der

doi:10.1016/j.tet.2014.01.035

Cited by 16 publications

(11 citation statements)

References 86 publications

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“…After purification by column chromatography on silica (isohexane/EtOAc 8:2), 2b (782 mg, 85%) was obtained as a white solid: mp 68–69 °C; 1 H NMR (400 MHz, CDCl 3 ) δ 7.85–7.77 (m, 3H, Ar), 7.69 (s, 1H, Ar), 7.51–7.41 (m, 2H, Ar), 7.37 (dd, J = 8.4, 1.7 Hz, 1H, Ar), 3.96 (q, J = 6.0 Hz, 2H, CH 2 ), 3.04 (t, J = 6.5 Hz, 2H, CH 2 ), 1.43 (s, 1H, OH) ppm; 13 C{ 1 H} NMR (101 MHz, CDCl 3 ) δ 136.08, 133.72, 132.44, 128.42, 127.79, 127.63, 127.62, 127.52, 126.25, 125.62, 63.70, 39.51 ppm; HRMS (EI) m / z [M] + calcd for C 12 H 12 O 172.0888, found 172.0880. The 1 H/ 13 C{ 1 H} NMR spectra are in full agreement with them reported in literature …”

Section: Methodssupporting

confidence: 89%

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Size-Driven Inversion of Selectivity in Esterification Reactions: Secondary Beat Primary Alcohols

2021

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Relative rates for the Lewis base-mediated acylation of secondary and primary alcohols carrying large aromatic side chains with anhydrides differing in size and electronic structure have been measured. While primary alcohols react faster than secondary ones in transformations with monosubstituted benzoic anhydride derivatives, relative reactivities are inverted in reactions with sterically biased 1-naphthyl anhydrides. Further analysis of reaction rates shows that increasing substrate size leads to an actual acceleration of the acylation process, the effect being larger for secondary as compared to primary alcohols. Computational results indicate that acylation rates are guided by noncovalent interactions (NCIs) between the catalyst ring system and the DED substituents in the alcohol and anhydride reactants. Thereby stronger NCIs are formed for secondary alcohols than for primary alcohols.

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Section: Methodssupporting

confidence: 89%

“…The 1 H/ 13 C{ 1 H} NMR spectra are in full agreement with them reported in literature. 20 1-(Pyren-1-yl)ethan-1-ol 1d. In a Schlenk flask, pyrene-1carbaldehyde (2.00 g, 8.69 mmol, 1.0 equiv) was dissolved in THF (11 mL).…”

Section: ■ Conclusionmentioning

confidence: 99%

Size-Driven Inversion of Selectivity in Esterification Reactions: Secondary Beat Primary Alcohols

2021

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“…1.2-di(thiophenyl)ethane-1.2-diol ( meso ): 1 H-NMR (500 MHz, CDCl 3 ): δ 5.13 (2H, s), 6.81–7.28 (6H, m). Chemical shifts were in accordance with the literature [36,39].…”

Section: Methodssupporting

confidence: 59%

Hydrogenations without Hydrogen: Titania Photocatalyzed Reductions of Maleimides and Aldehydes

et al. 2014

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Abstract:A mild procedure for the reduction of electron-deficient alkenes and carbonyl compounds is described. UVA irradiations of substituted maleimides with dispersions of titania (Aeroxide P25) in methanol/acetonitrile (1:9) solvent under dry anoxic conditions led to hydrogenation and production of the corresponding succinimides. Aromatic and heteroaromatic aldehydes were reduced to primary alcohols in similar titania photocatalyzed reactions. A mechanism is proposed which involves two proton-coupled electron transfers to the substrates at the titania surface.

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“…We have introduced the step of the colored photoisomer 2 deprotona- tion into the revised mechanism of diarylethene 1 photorearrangement (Scheme 2). The similar heterolytic cleavage of a substituent on the reactive carbon of the photoinduced isomer was considered recently for base-induced reactions of 2-(fur-3-yl)ethenylarenes 53 and nucleophile-induced rearrangements of photochromic diarylethenes. 54 For additional confirmation of the proposed mechanism, we studied the influence of bases on the stability of photoisomer 10 of diarylethene 9 (Scheme 5).…”

Section: (T) 1(t) 1(s ) 1(s)mentioning

confidence: 74%

Mechanistic Aspects of Photoinduced Rearrangement of 2,3-Diarylcyclopentenone Bearing Benzene and Oxazole Moieties

et al. 2018

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Photoinduced rearrangement of diarylethenes to naphthalenes or isoelectronic benzoannulated heterocycles is a novel reaction in preparative organic photochemistry. Recently it was shown that unsymmetrical diarylethenes containing benzene and oxazole derivatives efficiently undergo this transformation leading to amide derivatives of naphthalene. Mechanistic study of skeletal rearrangement for a typical representative of these compounds, namely 3-(5-methyl-2-phenyl-1,3-oxazol-4-yl)-2-phenylcyclopent-2-en-1-one, was performed by stationary and laser flash photolysis as well as density functional theory (DFT) calculations. The mechanism of the rearrangement was found to comprise several thermal stages. Both singlet and triplet states of the initial compound can be transformed to the reaction product, which results in the dependence of the quantum yield vs concentration of dissolved oxygen. Three reactive intermediates were registered in the laser flash photolysis experiment; the predicted structures were in accordance with DFT calculations of the electronic absorption spectra. In addition to the previously proposed mechanism of skeletal rearrangement based on a sigmatropic shift of hydrogen, two new parallel pathways based on formation of a carbanion/carbocation were determined.

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Construction of polyaromatics via photocyclization of 2-(fur-3-yl)ethenylarenes, using a 3-furyl group as an isopropenyl equivalent synthon

Cited by 16 publications

References 86 publications

Size-Driven Inversion of Selectivity in Esterification Reactions: Secondary Beat Primary Alcohols

Size-Driven Inversion of Selectivity in Esterification Reactions: Secondary Beat Primary Alcohols

Hydrogenations without Hydrogen: Titania Photocatalyzed Reductions of Maleimides and Aldehydes

Mechanistic Aspects of Photoinduced Rearrangement of 2,3-Diarylcyclopentenone Bearing Benzene and Oxazole Moieties

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