Isolation and chemistry of the invertomers of N-chlorobenzoylphenylaziridine

Opposite Regiospecific Ring Opening of 2-(Cyanomethyl)aziridines by Hydrogen Bromide and Benzyl Bromide: Experimental Study and Theoretical Rationalization

“…Pyramidal inversion at the nitrogen center of amines is known to occur at a fast rate, preventing a permanent chiral center on the nitrogen atom and hence not allowing the isolation of invertomers (inversion isomers). However, there are literature studies in which invertomers have been isolated by slowing down the inversion rate through the use of large central atoms (P and As) or by the inclusion of a heteroatom in a small ring, as seen in certain aziridines . Increased angle strain in the aziridine ring is known to lead to an increased barrier for nitrogen inversion, in some cases high enough for the isolation of separate invertomers.…”

“…However, there are literature studies in which invertomers have been isolated by slowing down the inversion rate through the use of large central atoms (P and As) or by the inclusion of a heteroatom in a small ring, as seen in certain aziridines. 56 Increased angle strain in the aziridine ring is known to lead to an increased barrier for nitrogen inversion, in some cases high enough for the isolation of separate invertomers. For this reason, pyramidal inversion at the ring nitrogen of 1-arylmethyl-2-(cyanomethyl)aziridines 1 was computationally investigated, in order to verify the possibility of invertomer resolution (Scheme 3).…”