The Quest for Stable Silaaldehydes: Synthesis and Reactivity of a Masked Silacarbonyl

Debotra Sarkar; Vitaly Nesterov; Tibor Szilvási; Philipp J. Altmann; Shigeyoshi Inoue

doi:10.1002/chem.201805604

The Quest for Stable Silaaldehydes: Synthesis and Reactivity of a Masked Silacarbonyl

Debotra Sarkar, Vitaly Nesterov, Tibor Szilvási, Philipp J. Altmann, Shigeyoshi Inoue

Professur für Siliciumchemie

Publikation: Beitrag in Fachzeitschrift › Artikel › Begutachtung

29 Zitate (Scopus)

Abstract

The first donor–acceptor complex of a silaaldehyde, with the general formula (NHC)(Ar)Si(H)OGaCl₃ (NHC=N-heterocyclic carbene), was synthesized using the reaction of silyliumylidene–NHC complex [(NHC)₂(Ar)Si]Cl with water in the presence of GaCl₃. Conversion of this complex to the corresponding silacarboxylate dimer [(NHC)(Ar)SiO₂GaCl₂]₂, free silaacetal ArSi(H)(OR)₂, silaacyl chloride (NHC)(Ar)Si(Cl)OGaCl₃, and phosphasilene–NHC adduct (NHC)(Ar)Si(H)PTMS unveil its true potential as a synthon in silacarbonyl chemistry.

Originalsprache	Englisch
Seiten (von - bis)	1198-1202
Seitenumfang	5
Fachzeitschrift	Chemistry - A European Journal
Jahrgang	25
Ausgabenummer	5
DOIs	https://doi.org/10.1002/chem.201805604
Publikationsstatus	Veröffentlicht - 24 Jan. 2019

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10.1002/chem.201805604

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title = "The Quest for Stable Silaaldehydes: Synthesis and Reactivity of a Masked Silacarbonyl",

abstract = "The first donor–acceptor complex of a silaaldehyde, with the general formula (NHC)(Ar)Si(H)OGaCl3 (NHC=N-heterocyclic carbene), was synthesized using the reaction of silyliumylidene–NHC complex [(NHC)2(Ar)Si]Cl with water in the presence of GaCl3. Conversion of this complex to the corresponding silacarboxylate dimer [(NHC)(Ar)SiO2GaCl2]2, free silaacetal ArSi(H)(OR)2, silaacyl chloride (NHC)(Ar)Si(Cl)OGaCl3, and phosphasilene–NHC adduct (NHC)(Ar)Si(H)PTMS unveil its true potential as a synthon in silacarbonyl chemistry.",

keywords = "N-heterocyclic carbenes, silaaldehydes, silacarbonyl groups, silanones, silyliumylidenes",

author = "Debotra Sarkar and Vitaly Nesterov and Tibor Szilv{\'a}si and Altmann, {Philipp J.} and Shigeyoshi Inoue",

note = "Publisher Copyright: {\textcopyright} 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

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doi = "10.1002/chem.201805604",

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T1 - The Quest for Stable Silaaldehydes

T2 - Synthesis and Reactivity of a Masked Silacarbonyl

AU - Sarkar, Debotra

AU - Nesterov, Vitaly

AU - Szilvási, Tibor

AU - Altmann, Philipp J.

AU - Inoue, Shigeyoshi

PY - 2019/1/24

Y1 - 2019/1/24

N2 - The first donor–acceptor complex of a silaaldehyde, with the general formula (NHC)(Ar)Si(H)OGaCl3 (NHC=N-heterocyclic carbene), was synthesized using the reaction of silyliumylidene–NHC complex [(NHC)2(Ar)Si]Cl with water in the presence of GaCl3. Conversion of this complex to the corresponding silacarboxylate dimer [(NHC)(Ar)SiO2GaCl2]2, free silaacetal ArSi(H)(OR)2, silaacyl chloride (NHC)(Ar)Si(Cl)OGaCl3, and phosphasilene–NHC adduct (NHC)(Ar)Si(H)PTMS unveil its true potential as a synthon in silacarbonyl chemistry.

AB - The first donor–acceptor complex of a silaaldehyde, with the general formula (NHC)(Ar)Si(H)OGaCl3 (NHC=N-heterocyclic carbene), was synthesized using the reaction of silyliumylidene–NHC complex [(NHC)2(Ar)Si]Cl with water in the presence of GaCl3. Conversion of this complex to the corresponding silacarboxylate dimer [(NHC)(Ar)SiO2GaCl2]2, free silaacetal ArSi(H)(OR)2, silaacyl chloride (NHC)(Ar)Si(Cl)OGaCl3, and phosphasilene–NHC adduct (NHC)(Ar)Si(H)PTMS unveil its true potential as a synthon in silacarbonyl chemistry.

KW - N-heterocyclic carbenes

KW - silaaldehydes

KW - silacarbonyl groups

KW - silanones

KW - silyliumylidenes

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DO - 10.1002/chem.201805604

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AN - SCOPUS:85058979512

SN - 0947-6539

VL - 25

SP - 1198

EP - 1202

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 5

ER -

The Quest for Stable Silaaldehydes: Synthesis and Reactivity of a Masked Silacarbonyl

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