Substitution reactions in the acenaphthene analog of quino[7,8-h]quinoline and an unusual synthesis of the corresponding acenaphthylenes by tele-elimination

• Ekaterina V. Kolupaeva,
• Narek A. Dzhangiryan,
• Alexander F. Pozharskii,
• Oleg P. Demidov and
• Valery A. Ozeryanskii

Beilstein J. Org. Chem. 2024, 20, 243–253, doi:10.3762/bjoc.20.24

• reaction with neutral or anionic bases. Keywords: dipyrido[3,2-e:2′,3′-h]acenaphthene (acenaphthylene); hydrogen bonding; π-stacking; substitution reactions; tele-elimination; Introduction Quinoline derivatives, classical nitrogen-containing heterocycles, are widely distributed in nature in various forms

• activity/inactivity in amination reactions. It is known that acenaphthylenes are usually readily formed from acenaphthenes by dehydrogenation with chloranil, dichlorodicyanobenzoquinone (DDQ) or active MnO2 on reflux in toluene/xylene and other inert solvents. However, attempts to obtain acenaphthylene 8

• , it became obvious that the second component formed in the dinitration reaction is not the mononitro derivative 11, but acenaphthylene 12 (Figure 6). To prove this hypothesis, as well as to compare the ease of dehydrogenation of dinitroacenaphthene 10 with respect to the initial substrate 5, it was

Recent synthesis of thietanes

• Jiaxi Xu

Beilstein J. Org. Chem. 2020, 16, 1357–1410, doi:10.3762/bjoc.16.116

• nm UV light [63]. In 1978, Gotthardt and Nieberl investigated the UV light-induced [2 + 2] cycloaddition reaction of thiones with cyclic alkenes and realized the synthesis of spirothietane derivatives. Under n → π* excitation using Na light, xanthione (196) reacted with acenaphthylene (197), indene

Dialkyl dicyanofumarates and dicyanomaleates as versatile building blocks for synthetic organic chemistry and mechanistic studies

• Grzegorz Mlostoń and
• Heinz Heimgartner

Beilstein J. Org. Chem. 2017, 13, 2235–2251, doi:10.3762/bjoc.13.221

• ]. Dialkyl dicyanofumarates E-1 form also CT complexes with electron-rich non-conjugated dienes such as hexamethyl Dewar benzene [77][78], as well as indene and acenaphthylene [79]. These complexes were used for photochemical studies, e.g., the photoisomerization of Dewar benzenes into the corresponding

Cross-linked cyclodextrin-based material for treatment of metals and organic substances present in industrial discharge waters

• Élise Euvrard,
• Nadia Morin-Crini,
• Coline Druart,
• Justine Bugnet,
• Bernard Martel,
• Cesare Cosentino,
• Virginie Moutarlier and
• Grégorio Crini

Beilstein J. Org. Chem. 2016, 12, 1826–1838, doi:10.3762/bjoc.12.172

• PAHs: naphthalene (NAP), acenaphthene (ACE), acenaphthylene (ACY), fluorene (FLU), phenanthrene (PHE), anthracene (ANT), fluoranthene (FLT) and pyrene (PYR); eight heavy PAHs: benz[a]anthracene (BaANT), chrysene (CHY), benzo[b]fluoranthene (BbFLT), benzo[k]fluoranthene (BkFLT), benzo[a]pyrene (BaPYR

Topochemical control of the photodimerization of aromatic compounds by γ-cyclodextrin thioethers in aqueous solution

• Hai Ming Wang and
• Gerhard Wenz

Beilstein J. Org. Chem. 2013, 9, 1858–1866, doi:10.3762/bjoc.9.217

• aromatic guests under controlled, homogenous reaction conditions. The quantum yields for unsubstituted anthracene, acenaphthylene, and coumarin complexed in these γ-CD thioethers were found to be up to 10 times higher than in the non-complexed state. The configuration of the photoproduct reflected the

• configuration of the dimeric inclusion complex of the guest. Anti-parallel orientation of acenaphthylene within the CD cavity led to the exclusive formation of the anti photo-dimer in quantitative yield. Parallel orientation of coumarin within the complex of a CD thioether led to the formation of the syn head

• -to-head dimer. The degree of complexation of coumarin could be increased by employing the salting out effect. Keywords: acenaphthylene; anthracene; coumarin; cyclodextrins; photodimerization; quantum yield; stereoselectivity; Introduction Photochemical reactions have been considered highly

Molecular solubilization of fullerene C₆₀ in water by γ-cyclodextrin thioethers

• Hai Ming Wang and
• Gerhard Wenz

Beilstein J. Org. Chem. 2012, 8, 1644–1651, doi:10.3762/bjoc.8.188

• anthracene and acenaphthylene, in water [33][34][35]. In this work, we investigated solubilization of C60 by these γ-CD thioethers (compounds 1–7 in Scheme 1) with the hope of achieving high concentrations of solubilized C60. The hydrophilic substituents at the primary face of γ-CD should increase solubility

Chromo- and fluorophoric water-soluble polymers and silica particles by nucleophilic substitution reaction of poly(vinyl amine)

• Katja Hofmann,
• Ingolf Kahle,
• Frank Simon and
• Stefan Spange

Beilstein J. Org. Chem. 2010, 6, No. 79, doi:10.3762/bjoc.6.79

• material acenaphthylene-1,2-dione undergoes a Knoevenagel condensation with malononitrile to give mono-adduct 2. Compound 2 was originally synthesized by Junek et al. [38]. However, no detailed NMR data were reported. In a second step, cyclization with anhydrous K2CO3 converted 2 to 1 in a good yield. In

• Chemie (Burghausen, Germany). 2-(2-Oxo-2H-acenaphthylene-1-ylidene)-malononitrile (2) Compound 2 was synthesized as described earlier [34]. Acenaphthene-1,2-dione (2.00 g, 11 mmol) and malononitrile (0.73 g, 11 mmol) were dissolved in 40 mL of CH3CN and refluxed for 3 h. After cooling, the orange

• -Oxo-8H-acenaphtho[1,2-b]pyrrol-9-carbonitrile (1) 2-(2-Oxo-2H-acenaphthylene-1-ylidene)-malononitrile (2) (0.80 g, 3.5 mmol) and K2CO3 (48 mg, 0.35 mmol) in 5 mL of CH3CN were refluxed for 1 h. After cooling, the yellow-orange precipitate was filtered off and washed several times with CH3CN to yield 1