Reaction of dimethyl(chloromethyl)chlorosilane with trimethylsilyl derivatives of l-phenyl-2-acetyl- and 1-phenyl-2-trifluoroacetylhydrazines

Kalikhman, I. D.; Bannikova, O. B.; Волкова, Л. И.; Belousova, L. I.; Yushmanova, T. I.; Лопырев, В. А.; Vyazankina, O. A.; Vyazankin, N. S.; Pestunovich, V. A.

doi:10.1007/bf01474219

Cited by 2 publications

(2 citation statements)

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“…Reactions of N,N-dimethylhydrazonates 302 with dimethyldichlorosilane and dimethylchlorosilane yielded 2,2-dimethyl-2-substituted-5-substituted-1-oxa-4-aza-2silacyclopent-4-enes 304 and the corresponding ring system 305, respectively [172,[175][176][177][178][179].…”

Section: Synthesis Of Silicon Hexacoordinate Chelatesmentioning

confidence: 99%

The Chemistry of Hydrazonates

Shawali¹,

Sherif

2007

COC

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The chemistry of esters of hydrazonoic acids has gained increased interest in both synthetic organic chemistry and biological fields. Since a large number of developments in the use of such esters, a review of such developments, covering the literature up to mid 2005, seems to be of considerable value. The present review presents their structural features, nomenclature, synthetic methods and chemical reactions. The utility of the latter reactions for synthesis of various heterocyclic ring systems including mono-, bi-, tri-, tetra-, and penta-heterocycles. In addition, their silicon chelates and biological applications are presented.

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Section: Synthesis Of Silicon Hexacoordinate Chelatesmentioning

confidence: 99%

The Chemistry of Hydrazonates

Shawali¹,

Sherif

2007

COC

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“…Hypercoordinate organosilicon compounds have attracted considerable attention in recent years . One effective route leading to O→Si pentacoordinate silicon complexes consists of the reaction of chloro(chloromethyl)dimethylsilane (ClCH 2 SiMe 2 Cl, 1 ) with various N - or O -trimethylsilylamides, , lactams, , acetylacetamide, and 2-pyridones, , as shown, for example, in eq . The reaction is a two-step process: transsilylation, followed by internal nucleophilic displacement of chloride by nitrogen or oxygen. …”

Section: Introductionmentioning

confidence: 99%

Regioselective Intramolecular Chloride Displacement Leading to Five- or Six-Membered Chelate-Ring Closure and Pentacoordinate Silicon Complexes: A Facile Wawzonek Rearrangement

et al. 2009

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O-Trimethylsilylated hydrazides with Schiff-base derivatives at the terminal nitrogen atoms-[RC(OSiMe 3 )dNNdCR 0 R 00 ] react with chloro(chloromethyl)dimethylsilane [ClCH 2 SiMe 2 Cl] in a regioselective manner, forming either five-membered or zwitterionic six-membered chelate complexes with pentacoordinate silicon. The type of product is determined by the size of the acidsubstituent R: bulky R groups (Ph, t-Bu) lead to exclusive formation of the six-membered product, whereas with the less bulky groups (Me, PhCH 2 ) only the five-membered product is obtained. Upon mild heating, the six-membered chelate complex transforms into its five-membered isomer, through a Wawzonek-type rearrangement. This facile transformation is remarkable in comparison to previously reported Wawzonek reactions that take place only at elevated temperatures. † Dedicated to Prof. Gerhard Roewer on the occasion of his 70th birthday.

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Reaction of dimethyl(chloromethyl)chlorosilane with trimethylsilyl derivatives of l-phenyl-2-acetyl- and 1-phenyl-2-trifluoroacetylhydrazines

Cited by 2 publications

References 4 publications

The Chemistry of Hydrazonates

The Chemistry of Hydrazonates

Regioselective Intramolecular Chloride Displacement Leading to Five- or Six-Membered Chelate-Ring Closure and Pentacoordinate Silicon Complexes: A Facile Wawzonek Rearrangement

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