Photochemically assisted synthesis of phenacenes fluorinated at the terminal benzene rings and their electronic spectra

• Yuuki Ishii,
• Minoru Yamaji,
• Fumito Tani,
• Kenta Goto,
• Yoshihiro Kubozono and
• Hideki Okamoto

Beilstein J. Org. Chem. 2025, 21, 670–679, doi:10.3762/bjoc.21.53

• , most likely due to different crystalline packing motifs. Keywords: fluorescence; fluorinated aromatics; phenacene; photoreaction; Introduction Polycyclic aromatic hydrocarbons (PAHs) have been subject of continuous interest not only from aspects of fundamental synthetic, structural, and physical

Asymmetric organocatalytic synthesis of chiral homoallylic amines

• Nikolay S. Kondratyev and
• Andrei V. Malkov

Beilstein J. Org. Chem. 2024, 20, 2349–2377, doi:10.3762/bjoc.20.201

• (trifluoromethylphenyl) group with other fluorinated aromatics (86–90) showed a gradual decrease in ee (92% ee in 90 to 68% ee in 86 and 88) depending on the degree of fluorination. Computational modelling for the 3,5-bis(trifluoromethylphenyl) catalyst 78 revealed that π-stacking interactions of the 4-pyrene group with

Utilizing the σ-complex stability for quantifying reactivity in nucleophilic substitution of aromatic fluorides

• Magnus Liljenberg,
• Tore Brinck,
• Tobias Rein and
• Mats Svensson

Beilstein J. Org. Chem. 2013, 9, 791–799, doi:10.3762/bjoc.9.90

• these investigations and the general requirements for predictive reactivity models for the pharmaceutical industry. We also present new results regarding the reaction rates and regioselectivities in nucleophilic substitution of fluorinated aromatics. They were rationalized by investigating linear

• ) followed by elimination of the leaving group [6]. In the case of attack of anionic nucleophiles (such as MeO−) on fluorinated aromatics, the intermediate σ-complex is anionic and the leaving group is F−, whereas in the case of neutral nucleophiles (such as NH3) the intermediate σ-complex is zwitterionic

• a number of 4-substituted 1-chloro-2-nitrobenzenes [21]. There are also many studies dealing with the formulation of empirical rules concerning reactivity in the nucleophilic substitution of fluorinated aromatics [22][23][24][25]. The nature of the empirical rules that typically emerge can be