110943-24-3Relevant academic research and scientific papers
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.
9-ALKENYLCARBAZOLES. XII. ELECTROPHILIC OXIDATION WITH MONOPERPHTHALIC ACID
Anfinogenov, V. A.,Malkova, N. N.,Sirotkina, E. E.,Filimonov, V.D.
, p. 2158 - 2163 (2007/10/02)
The oxidation of 9-alkenylcarbazoles by monoperphthalic acid takes place at the C=C bond with the formation of 9-(1-phthaloyloxy-2-hydroxyalkyl)carbazoles.The reactivity of the substances during oxidation agrees well with data on the reactivity in other electrophilic addition reactions and varies in line with the variation of the electron density at the β-carbon atom of the C=C bond.In the presence of methanol the oxidation of 9-alkenylcarbazoles with monoperphthalic acid leads to the formation of the diastereomers of 9-(1-methoxy-2-hydroxyalkyl)-carbazoles.
