DFT calculations induced a regiochemical outcome revision of the Diels-Alder reaction between levoglucosenone and isoprene

An appealing inversion in the regiochemical outcome of Diels-Alder reactions between levoglucosenone (1) and its α-bromo derivative (5) with isoprene (2) was studied computationally. Based on different DFT calculations we concluded that both reactions should display the same regioselectivity. This r...

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Detalhes bibliográficos
Autores: Sarotti, Ariel Marcelo, Suarez, Alejandra Graciela, Spanevello, Rolando Angel
Formato: artículo
Estado:Versión publicada
Fecha de publicación:2011
País:Argentina
Recursos:Consejo Nacional de Investigaciones Científicas y Técnicas
Repositorio:CONICET Digital (CONICET)
Idioma:inglés
OAI Identifier:oai:ri.conicet.gov.ar:11336/127148
Acesso em linha:http://hdl.handle.net/11336/127148
Access Level:acceso abierto
Palavra-chave:DFT
DIELS-ALDER
LEVOGLUCOSENONE
REGIOCHEMISTRY
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
Descrição
Resumo:An appealing inversion in the regiochemical outcome of Diels-Alder reactions between levoglucosenone (1) and its α-bromo derivative (5) with isoprene (2) was studied computationally. Based on different DFT calculations we concluded that both reactions should display the same regioselectivity. This result was further validated experimentally.

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