Mechanism of One-Pot Stereoselective Assembly of Spiroketal Derivatives from Cyclohexanone and Phenylacetylene in KOH/DMSO: a Quantum Chemical Study

V. B. Orel; Орел В. Б.; A. A. Manzhueva; Манжуева А. А.

doi:10.31857/S0207401X23070154

Mechanism of One-Pot Stereoselective Assembly of Spiroketal Derivatives from Cyclohexanone and Phenylacetylene in KOH/DMSO: a Quantum Chemical Study

Authors: Orel V.B.¹, Manzhueva A.A.¹
Affiliations:
1. Irkutsk State University
Issue: Vol 42, No 7 (2023)
Pages: 59-69
Section: XXXIV СИМПОЗИУМ “СОВРЕМЕННАЯ ХИМИЧЕСКАЯ ФИЗИКА” (СЕНТЯБРЬ 2022 г., ТУАПСЕ)
URL: https://rjmseer.com/0207-401X/article/view/674853
DOI: https://doi.org/10.31857/S0207401X23070154
EDN: https://elibrary.ru/YFNJBE
ID: 674853

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Abstract

The formation mechanisms of 15-[(Z)-phenylmethylidene]-7,14-dioxadispiro[5.1.5.2]pentadecane and the competitive formation of unsaturated ketones from cyclohexanone and phenylacetylene are studied using the B2PLYP-D2/6-311+G**//B3LYP/6-31+G* quantum chemical approach, taking into account solvation effects within the IEFPCM model. All stages of the assembly of dispiroketal and the stability of various conformers and isomers of the intermediates and the product are considered using the anionic model (ANIONGAS). Within the more detailed MONOPCM model, the activation barriers of the assembly of dispiroketal and the competing reaction of C-vinylation are evaluated. The obtained results of the quantum chemical calculations are in close agreement with the experimental data.

Keywords

spiroketals, cycloaliphatic ketones, superbase, quantum chemical calculations

About the authors

V. B. Orel

Irkutsk State University

Email: orelv@isu.ru
Irkutsk, Russia

A. A. Manzhueva

Irkutsk State University

Author for correspondence.
Email: orelv@isu.ru
Irkutsk, Russia

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