Inductive Hydroxyhalogenation of Bicyclo[2.2.1]heptenes and Synthesis of Amino Alcohols from the Reaction Products

Sadygov, O. A.; Alimardanov, Kh. M.; Ismailova, Sh. I.

doi:10.1134/s1070363218050031

Cited by 2 publications

(1 citation statement)

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“…Hydroxychloro(bromo)ide acid of these cyclo-olefins are obtained by the previously developed method [4,5]. In this case, the synthesis process is carried out sequentially in several stages, with the formation of hydroxychloro-2 (a-d) and hydroxybromide-3 (a-d) according to the scheme:…”

Section: Introductionmentioning

confidence: 99%

Conformational Aspects of the Reaction Products of Oxidative Hydroxyhalogenation of Alkyl Cyclohexenes

Ismayilova¹

2019

Chemical Problems

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The kinetic patterns of the reaction oxidative hydroxyhalogenated alkylcyclohexenes involving hydrogen peroxide and hydrogen halide acids in the liquid phase are considered. The reaction is reversible and has a second order in the forward and reverse directions. The speed of both stages of the process is correlated with the conformational effects of the substituents. The optimal reaction conditions were established and the isomeric and conformational composition of the obtained products was determined. The results of the kinetic studies and the study of stereochemistry and conformational equilibrium of the obtained adducts suggest that this reaction proceeds according to the electrophilic mechanism with the formation of trans-addition products. It was found that in the equilibrium mixture of reaction adducts, there are mainly conformers with an axial arrangement of a halogen atom and a hydroxyl group with an equatorial position of the substituents. Based on kinetic and spectral data, a probable reaction mechanism and conformer structure are proposed.

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Section: Introductionmentioning

confidence: 99%