Tayama, Eiji; Kawai, Kohei published the artcile< Synthesis of tertiary alkyl fluorides and chlorides by site-selective nucleophilic ring-opening reaction of α-aryl azetidinium salts>, Electric Literature of 3959-07-7, the main research area is chloride alkyl fluoride preparation regioselective; aryl azetidinium salt nucleophilic ring opening.
Site-selective nucleophilic ring-opening reactions of 2-arylazetidine-2-carboxylic acid ester-derived tetraalkyl ammonium salts with tetrabutylammonium halides (Bu4NX) to give tertiary alkyl halides I [R = 5-Me, 5-MeO, 3-Br, 4-Br, 5-Br, 4-CF3, 5-CF3; R1 = NEt2, F, Cl; R2 = NEt2, F, Cl] were successfully demonstrated. For example, a nucleophilic ring-opening reaction of 2-(o-tolyl) derivative with 1.2 equiv of tetrabutylammonium fluoride (Bu4NF) in THF at 60°C preferentially proceeded at a more substituted carbon atom (2-position) compared to a less-substituted carbon atom (4-position) and afforded tert-Bu 4-(dimethylamino)-2-fluoro-2-(o-tolyl)butanoate in 71% yield as the corresponding tertiary alkyl fluoride. This result was applied to synthesize optically active organofluorine compounds starting from com. available (R)-1-phenylethylamine.
RSC Advances published new progress about Azetidines Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation) (aryl). 3959-07-7 belongs to class bromides-buliding-blocks, and the molecular formula is C7H8BrN, Electric Literature of 3959-07-7.
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary