, volume 52 , issue 15 , pages 2147-2161

Manifestation of the β-Silicon Effect in the Reactions of Unsaturated Systems Involving a 1,2-Silyl Shift

Māris Turks ¹

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Institute of Technology of Organic Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University |

Publication type: Journal Article

Publication date: 2020-04-20

Georg Thieme Verlag KG

Synthesis

scimago Q2

wos Q2

SJR: 0.559

CiteScore: 4.6

Impact factor: 2.3

ISSN: 00397881, 1437210X

DOI: 10.1055/s-0039-1690898

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Catalysis

Organic Chemistry

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

Found

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Turks M. Manifestation of the β-Silicon Effect in the Reactions of Unsaturated Systems Involving a 1,2-Silyl Shift // Synthesis. 2020. Vol. 52. No. 15. pp. 2147-2161.

GOST all authors (up to 50) Copy

Turks M. Manifestation of the β-Silicon Effect in the Reactions of Unsaturated Systems Involving a 1,2-Silyl Shift // Synthesis. 2020. Vol. 52. No. 15. pp. 2147-2161.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1055/s-0039-1690898

UR - https://doi.org/10.1055/s-0039-1690898

TI - Manifestation of the β-Silicon Effect in the Reactions of Unsaturated Systems Involving a 1,2-Silyl Shift

T2 - Synthesis

AU - Turks, Māris

PY - 2020

DA - 2020/04/20

PB - Georg Thieme Verlag KG

SP - 2147-2161

IS - 15

VL - 52

SN - 0039-7881

SN - 1437-210X

ER -

BibTex |

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BibTex (up to 50 authors) Copy

@article{2020_Turks,

author = {Māris Turks},

title = {Manifestation of the β-Silicon Effect in the Reactions of Unsaturated Systems Involving a 1,2-Silyl Shift},

journal = {Synthesis},

year = {2020},

volume = {52},

publisher = {Georg Thieme Verlag KG},

month = {apr},

url = {https://doi.org/10.1055/s-0039-1690898},

number = {15},

pages = {2147--2161},

doi = {10.1055/s-0039-1690898}

}

MLA

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MLA Copy

Turks, Māris. “Manifestation of the β-Silicon Effect in the Reactions of Unsaturated Systems Involving a 1,2-Silyl Shift.” Synthesis, vol. 52, no. 15, Apr. 2020, pp. 2147-2161. https://doi.org/10.1055/s-0039-1690898.

Publisher

Georg Thieme Verlag KG

Journal

Synthesis

scimago Q2

wos Q2

SJR

0.559

CiteScore

4.6

Impact factor

2.3

ISSN

00397881 (Print)

1437210X (Electronic)