L. L. Sokova

Oxidation of 1-alkylcycloalkanols with PbIV and MnIII compounds under mechanical activation

A mechanoactivated solid-state oxidative decyclization of 1-alkylcycloalkanols under the action of the Pb(OAc)4−MX or Mn(OAc)3−MX systems (MX is a metal halide) was carried out for the first time. The reaction affords exclusively ω-haloalkanones.

Bromination of alkenols with the H2O2—LiBr—CeIII and H2O2—LiBr—CeIV systems

Reactions of alkenols with H2O2—LiBr—Ce(NO3)3·6H2O or H2O2—LiBr—Ce(NH4)2(NO3)6 system led to bromination of the double bond to yield vicinal dibromoalkanols. The reaction proceeded highly selectively, no oxidation of the hydroxyl group virtually occurred.

Primary alkanols: oxidative homocondensation in water and cross-condensation in methanol

Water was used as a reaction medium and a reagent in oxidation of primary alkanols to dimeric esters and alkanoic acids using either molecular bromine or a hydrogen peroxide—hydrobromic acid mixture as the oxidants. The similar reaction in methanol produced methyl alkanoates.

Bromination of ketones with the systems H2O2-LiBr-CeIII and H2O2-LiBr-CeIV

A new method for the synthesis of α-bromoketones was suggested. The C5-C11 linear and branched ketones in the reaction with the systems H2O2-LiBr-CeIII and H2O2-LiBr-CeIV in acetonitrile were brominated at α-position. The reaction is highly selective.

Solid-phase oxoalkylation of pyridines and quinolines with 1-methylcycloalkanols under the action of lead tetraacetate

A new procedure was developed for the introduction of the oxoalkyl fragment into N-heteroaromatic compounds of the pyridine and quinoline series. The procedure is based on the solid-phase reactions of lead tetraacetate with aromatic N-heterocycles and tertiary cycloalkanols.

Oxoalkylation of Pyrazine by 1-Methylcycloalkanols Upon Mechanical Activation

Solid-phase reactions and reactions in the absence of solvent have recently attracted considerable attention [1, 2]. We have already shown that the solid-phase reaction of protonated pyridine and 4-picoline with tertiary cyclic alcohols, which proceeds by the action of Pb(OAc)4, leads to the products of the oxoalkylation of these heterocyclic compounds in high yield [3]. However, the oxoalkylation of pyrazine could not be achieved under analogous conditions.

Electrochemical oxidative ring opening of 1-methylcyclobutanol

The manganese(III) acetate-mediated electrooxidative ring opening of 1-methylcyclobutanol (1) in acetic acid affords pentane-2-one (2) as the major product. The reaction of 1-methylcyclobutanol with Mn(OAc)3-LiCl gives 5-chloropentane-2-one (4.

solid-state reaction of a lead tetraacetate-metal halide system with naphthalene under mechanical activation

A mechanically activated solid-state reaction of halogenation of naphthalene with a Pb(OAc)4—alkaline or alkaline-earth metal halide system was carried out to yield 1-halonaphthalene as the main reaction product and 1,4-dihalonaphthalene. The solid-state halogenation of naphthalene is more selective than a liquid-phase reaction.

Homolytic oxoalkylation of protonatedN-heteroaromatic compounds

The oxoalkylation of pyridine, 2-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethylpyridines, quinoline, 4-methylquinoline, isoquinoline, and pyrazine with oxoalkyl radicals generated from 1-methylcyclobutanol or 1-methylcyclopentanol under the action of Pb(OAc)4 or Mn(OAc)3 has been carried out. The reaction products are isomers with 2-(6)- and 4-positions of the oxoalkyl group in theN-heteroaromatic ring. The isomer ratios have been determined as a function of the structure of theN-heteroaromatic compound and the reaction conditions.