Disilyldihydronaphthalenes from Alkali Metal Naphthalenides and Chlorosilanes

Abstract

March 1965 obtained, b.p. 107°( 25 mm.), b.p. 215°( 763 mm.) (lit. b.p. 211-213°, »"d 1.5312).Infrared spectrum showed bands at 9.81 (cyclopropyl), 3.27

Nucleophilic displacement versus electron transfer in the reactions of alkyl chlorosilanes with electrogenerated aromatic anion radicals

“…The ratio of these products is 1:1.7, the major isomer being supposedly 1,2-silylated one. These results agree with those observed for the reaction of chemically prepared naphthyl lithium with Me 3 SiCl [68] and Me 3 SiCN [69]. Interestingly, the recovery of starting naphthalene was reported in the chemical version of this process, presuming that the Naph  also intervenes as electron transfer reagent providing an electron for the reduction of intermediate monosilylated naphthyl radical to the corresponding anion [68].…”

Sonochemical Synthesis of Polysilylenes by Reductive Coupling of Disubstituted Dichlorosilanes with Alkali Metals

“…The use of sodium naphthalenide with Ph 3 SiCI and PhMe 2 SiCl has been previously reported to yield disilanes as the major products and a small amount of 1,4-bis(triphenylsilyl)-1,4-dihydronaphthalene 37 . However, in contrast to triphenylchlorosilane, the reaction of trimethylchlorosilane with sodium naphthalenide yields only 1,2-bis(trimethylsilyl)-1,4-dihydronaphthalene 38 . No hexamethyldisilane was obtained.…”

Synthesis and Structural Characterization of Isomeric Bis[3,4,5,6-tetrakis(trimethylsilyl)cyclohexen-1-yl]dimethoxysilanes

“…The syntheses of polysilylated cycles from aromatic precursors have been accomplished by Birch type reductive silylation [1][2][3][4][5][6][7][8][9][10][11][12][13][14] and electrochemical silylation. [15][16][17][18][19] Although the strategy of Birch type reductive silylation has several drawbacks vs electrochemical silylation such as using metal reducing agents, and irregular yields, it has been well developed as one of useful methods for the formation of carbon-silicon bonds in both carbon and organosilicon chemistry.…”