Work

In Silico Study on Chemical Properties and Reactivity of Enal Derivatives

Year: 2015

Type: article

Abstract: The chemical properties and reactivity of enals were explored by means of quantum chemical methods of calculation. The substituent effects were examined by analyzing the formation of oxonium and carbenium intermediates via protonation reactions as models for activation of enals. Considering the nucleophilic addition of organometallic reagents to enals as an important synthetic step, formation and reactivity of the anionic derived species were modeled computationally for the bis‐silylated enals and their subsequent reaction with model electrophiles, in order to gain insight into the regio‐ and stereoselectivity previously observed in electrophilic additions. Silylated enals exhibited interesting features based on the electronic and steric properties of silyl substituents. The present model computations could assist in the development of new synthetic applications for this class of compounds as they find wider synthetic application.

Source: European Journal of Organic Chemistry

DOI: 10.1002/ejoc.201500853

Authors: Gabriela L. Borosky, Kenneth K. Laali

Institutions: University of North Florida, Consejo Nacional de Investigaciones Científicas y Técnicas, Universidad Nacional de Córdoba

Language: English

Topic: Chemical Reaction Mechanisms

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: University of Florida, University of North Florida, Universidad Nacional de Córdoba, Consejo Nacional de Investigaciones Científicas y Técnicas, Universidad de Córdoba

OpenAlex ID: W1868033192

FWCI:

Cites: 52

Cited by: 1

Related to: 10