110943-24-3Relevant articles and documents
N-HETEROARYLETHYLENES. X. KINETICS AND MECHANISM OF THE OXIDATION OF 9-ALKENYLCARBAZOLES BY MONOPERPHTHALIC ACID
Anfinogenov, V. A.,Malkova, N. N.,Sirotkina, E. E.,Filimonov, V. D.
, p. 452 - 455 (2007/10/02)
The oxidation of 9-alkenylcarbazoles by monoperphthalic acid takes place through an intermediate asymmetric cyclic complex (9-alkenylcarbazole - peracid) with a larger proportion of bonding between the electrophilic oxygen atom of the peracid and the β-carbon atom of the vinyl group and the subsequent formation of a β-hydroxycarbenium-immonium ion, by-passing the stage with the formation of an α-oxide ring.The rate constants for the oxidation of trans-9-propenylcarbazoles correlate with the ?p constants of the substituents in the ring.Trans-β-alkyl substituents as the olefinic bond lead to a small increase in the oxidation rate.The same substituents at the cis position act in the opposite direction and greatly reduce the reaction rate.