Facile Ring Opening of Oxiranes with Aromatic Amines in Fluoro Alcohols

Silica Perchloric Acid Matrix Supported Ring Opening of Epoxide Under Microwave Radiation†

“…Thus, aromatic amines react selectively at the benzylic carbon of the styrene oxide with anti-Markovnikov addition due to less nucleophilicity. The carbocationic character at the benzylic position of the epoxide ring is demonstrated that an increase in polarity of the reaction medium by the use of fluoro alcohols 35 and ionic liquids 10 leads to selective nucleophilic attack in the absence of metal catalyst.…”

Synthesis of New Trifluoromethylated Hydroxyethylamine‐Based Scaffolds

“…In the case of poorly reactive aromatic amines, a variety of activators [26][27][28][29] have been introduced to facilitate the ringopening reaction. Fluorinated alcohols have also been used to promote this reaction, [30] and recently, Azizi et al reported epoxide ring opening with aliphatic amines in water without any catalyst. [31] Thus, we investigated ring opening reactions of epoxides 1 with amines in water without catalyst, using 1.1 equiv.…”

Self‐Promoted Nucleophilic Addition of Hexafluoro‐2‐propanol to Vinyl Ethers

“…Nevertheless, it has been shown that, because of its high hydrogen bond donor ability, HFIP can deactivate good nucleophiles such as aliphatic alcohols or amines, by means of acid-base interactions. [16] First, it has been checked than 3a is stable at room temperature in the presence of 1 equivalent of benzyl alcohol, which proves that the formation of acetals 2a and 3a are two competitive pathways. Then kinetic studies of the competition between HFIP and other alcohols (MeOH, BnOH, i-PrOH, TFE) were investigated.…”