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Synthesis 2020; 52(15): 2147-2161
DOI: 10.1055/s-0039-1690898
DOI: 10.1055/s-0039-1690898
short review
Manifestation of the β-Silicon Effect in the Reactions of Unsaturated Systems Involving a 1,2-Silyl Shift
This work was supported by a grant from Latvian Council of Science (grant No. LZP-2018/1-0315) and doctoral student grant from Riga Technical University (grant No. DOK.MLKF/19).Further Information
Publication History
Received: 31 January 2020
Accepted after revision: 30 March 2020
Publication Date:
20 April 2020 (online)
Abstract
Many chemical transformations of organosilicon compounds proceed due to the capability of silyl substituents to stabilize a positive charge in its β-position. This short review provides an overview of the present understanding of the β-silicon effect and focusses on the synthetic applications of 1,2-silyl shifts resulting from non-vertical stabilization of alkylcarbenium ions and vinyl cations. The reactions of silicon containing unsaturated starting materials, alkenes, allenes, and alkynes, involving β-silyl group stabilized cationic intermediates, transition metal carbenes, or vinylidene complexes will be discussed.
1 Introduction
2 Origins of the β-Silicon Effect
3 Reactions of Allenylsilanes
4 Reactions of Alkynes
4.1 Propargylsilanes
4.2 Alkynylsilanes
5 Reactions of Alkenes
5.1 Allylsilanes
5.2 Vinylsilanes
6 Conclusions
-
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