A general overview on the chemical and stereochemical behaviour of a wide range of stereodefined 2-silyl-1,3-dithianes, -1,3-dioxanes, -1,3-dioxolanes and -1,3-oxathiolanes is reported, when subjected to fluoride ion induced proto- and carbo-desilylation. Retention of configuration or epimerization appear depending either on the kind of the substituents on the aromatic ring, but also on the nature of heteroatoms in the silyl acetals, leading to envisage the occurence of a free carbanion or of an hypervalent silylated species.
Fluoride-induced proto- and carbo-desilylation of S,S-, O,O- and O,S-silylated acetals: an insight into the chemical and stereochemical reaction outcome / Antonella Capperucci;Mariafrancesca Fochi;Andrea Mazzanti;Salvatore Pollicino. - In: JOURNAL OF SULFUR CHEMISTRY. - ISSN 1741-5993. - ELETTRONICO. - 34:(2013), pp. 606-616. [10.1080/17415993.2013.795225]
Fluoride-induced proto- and carbo-desilylation of S,S-, O,O- and O,S-silylated acetals: an insight into the chemical and stereochemical reaction outcome
CAPPERUCCI, ANTONELLA;
2013
Abstract
A general overview on the chemical and stereochemical behaviour of a wide range of stereodefined 2-silyl-1,3-dithianes, -1,3-dioxanes, -1,3-dioxolanes and -1,3-oxathiolanes is reported, when subjected to fluoride ion induced proto- and carbo-desilylation. Retention of configuration or epimerization appear depending either on the kind of the substituents on the aromatic ring, but also on the nature of heteroatoms in the silyl acetals, leading to envisage the occurence of a free carbanion or of an hypervalent silylated species.I documenti in FLORE sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.