A general overview on the chemical and stereochemical behavior 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 appears to depend not only 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.

A. Capperucci, M. Fochi, A. Mazzanti, S. Pollicino (2013). 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. JOURNAL OF SULFUR CHEMISTRY, 34(6), 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

FOCHI, MARIAFRANCESCA;MAZZANTI, ANDREA;POLLICINO, SALVATORE
2013

Abstract

A general overview on the chemical and stereochemical behavior 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 appears to depend not only 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.
2013
A. Capperucci, M. Fochi, A. Mazzanti, S. Pollicino (2013). 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. JOURNAL OF SULFUR CHEMISTRY, 34(6), 606-616 [10.1080/17415993.2013.795225].
A. Capperucci; M. Fochi; A. Mazzanti; S. Pollicino
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/143282
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