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Dialkylaminodifluorosulfinium salts: XtalFluor-E and XtalFluor-M

Opened Access Dialkylaminodifluorosulfinium salts: XtalFluor-E and XtalFluor-M

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Autor: Franconetti García, Antonio
Departamento: Universidad de Sevilla. Departamento de Química orgánica
Fecha: 2013
Publicado en: Synlett, 24 (7), 891-892.
Tipo de documento: Artículo
Resumen: (A) Failure of Hydrocinnamyl Alcohol with XtalFluor-M: The reaction of hydrocinnamyl alcohol with 2 or 1 in acetonitrile provided an intractable mixture. For this reaction to proceed, the addition of exogenous sources of fluoride, such as Et3N·3HF or Et3N·2HF, was necessary (B) Halogenation of Alcohols with XtalFluor Reagents: Reaction of primary, secondary and tertiary alcohols with 1 using Et3N·3HF as a promoter gave the fluorinated nucleophilic substitution products. The addition order was a key parameter in this reaction. To obtain good selectivity and stereochemical integrity, 1,8-diazabicycloundec-7-ene (DBU) had to be used together with the fluorination agents. 5 A mixture of fluorinated bridged biphenyl systems has been obtained from 3-hydroxyspirodienones by means of a XtalFluor-E-promoted rearrangement. When compound 2 was used instead of compound 1, substrate decomposition was observed. 6 Chlorination, bromination and iodination reaction of primary alcohols in good yield ha...
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Cita: Franconetti García, A. (2013). Dialkylaminodifluorosulfinium salts: XtalFluor-E and XtalFluor-M. Synlett, 24 (7), 891-892.
Tamaño: 174.1Kb
Formato: PDF

URI: http://hdl.handle.net/11441/62903

DOI: 10.1055/s-0032-1318499

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