Artículo
Substitution reactions between arenethiolate anions and 1,3-dihalo-2,2-dimethylpropanes. Synthetic scope and mechanistic aspects
Fecha de publicación:
03/2011
Editorial:
Arkat USA
Revista:
Arkivoc - Archive for Organic Chemistry
ISSN:
1551-7004
e-ISSN:
1551-7012
Idioma:
Inglés
Tipo de recurso:
Artículo publicado
Clasificación temática:
Resumen
The synthetic scope of the reactions between benzenethiolate, 4-methoxybenzenethiolate, 2-naphthalenethiolate, and 2-pyridinethiolate anions with 1,3-dihalo-2,2-dimethylpropane was studied. These reactions render mono and disubstituted products from good to excellent yields. For all the substrates studied the monosubstituted halogenated product is the intermediate or the main product depending on the nature of the second leaving group. Aryl cyclopropyl sulfides were found as side products and their yields strongly depend on the base concentration (tert-BuOK). Finally, using neopentyl iodide as a model, the mechanism of these reactions was evaluated based on non-kinetic evidence, demonstrating that the reactions switch from SRN1 to polar SN2 according to the solvent employed. © ARKAT-USA, Inc.
Palabras clave:
Aliphatic Substitution
,
Arenethiolate Anions
,
Neopentyl Halides
Archivos asociados
Licencia
Identificadores
Colecciones
Articulos(INFIQC)
Articulos de INST.DE INVESTIGACIONES EN FISICO- QUIMICA DE CORDOBA
Articulos de INST.DE INVESTIGACIONES EN FISICO- QUIMICA DE CORDOBA
Citación
Barrionuevo, Cecilia Andrea; Argüello, Juan Elias; Peñeñory, Alicia Beatriz; Substitution reactions between arenethiolate anions and 1,3-dihalo-2,2-dimethylpropanes. Synthetic scope and mechanistic aspects; Arkat USA; Arkivoc - Archive for Organic Chemistry; 2011; 7; 3-2011; 245-259
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