Bis chlorodimethylsilyl ethane

The optimal conditions for this reaction employ the freshly prepared silyl hydrazone, from which residual f-butlydimethyl-silanol has been removed under vacuum, and its slow addition to molecular bromine or iodine and base in dichloromethane. Following the original work of Barton with simple hydrazones, optimal yields were obtained when )V -f-butyl-)V,)V,)V, )V -tetrame-thylguanidine (BTMG) was used as base (eqs 12 and 13). 

Organic Reactions, John Wiley Sons Inc. New York, 1948 Vol. 4, p. 378. 

Form Supplied in white, waxy solid with a sharp acid odor 96% pure. 

A list of General Abbreviations appears on the from Endpapers 

A further extension of this concept is shown in the 6-substituted 3-pyridinol synthesis described in eq 7. Treatment of condensation product (19) with 1 M HCl initiates Stabase deprotection that is followed by acid-catalyzed rearrangement of the resulting amino alcohol to pyridine (20).  

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The commercially available dichlorosilane, 1,2-bis(chlorodimethylsilyl)-ethane, converts primary amines (/) into stabase derivatives ... 

Bis(chlorodimethylsilyl)ethane, 87 Bis(l,2-dimethylpropyl)borane, 30 Bis(diphenylphosphono)ethane, 114... 

Treatment of aromatic aldehydes such as p-anisaldehyde with Zn-powder and l,2-bis(chlorodimethylsilyl)ethane 45 give Zn-carbene adducts such as 2096 which add readily to olefins such as cyclohexene [22, 26] or styrene [26] to give high yields of cyclopropanes such as 2097 and the oxide 47 [26]. Acetals such as 2098 react analogously with cyclohexene to afford the endo and exo cyclopropanes 2099 and 2100 [22, 27] (Scheme 13.11). 

Functionalized zinc carbenoids have been prepared from carbonyl compounds by an indirect strategy. The deoxygenation of a carbonyl compound to an organozinc carbenoid can be induced by a reaction with zinc and TMSCl. Therefore, the aldehyde or ketone, when treated with TMSCl or l,2-bis(chlorodimethylsilyl)ethane in the presence of an alkene, generates the cyclopropanation product. This method is quite effective for the production of alkoxy-substituted cyclopropane derivatives. A 55% yield of the... 

A reactor charged with 3-bromobenzylamine (109 mmol), 150 ml of CH2CI2, and triethylamine (217 mmol) was cooled in an ice bath and treated with 109 ml of 1 M l,2-bis(chlorodimethylsilyl)ethane dissolved in CH2CI2. During the addition, considerable precipitate formed. The ice bath was removed and the mixture stirred for 6.5 hours at ambient temperature. A white solid was isolated by filtration... 

Treatment of a variety of a,/i-unsaturated carbonyl compounds with zinc and 1,2-bis(chlorodimethylsilyl)ethane leads to the formation of organozinc carbenoids which may be trapped with olefins to give alkenyl- and arylcyclopropanes (equation 78)131. With... 

Motherwell and Roberts dicarbonyl coupling reaction19 can be improved by substituting l,2-bis(chlorodimethylsilyl)ethane for TMSC1. The intermediate organozinc carbenoids can be trapped with alkenes to produce cyclopropanes, as exemplified in the intramolecular case in equation 3. 

The organozinc carbenoids generated from aryl and a, -unsaturated carbonyl compounds with zinc and l,2-bis(chlorodimethylsilyl)ethane can be trapped intramolecularly to give cyclo-... 

The Mg/TMSCl combination in DMF is another reducing system to be thoroughly studied. When treated with this reducing system, aromatic carbonyl compounds are converted into a-trimethylsilylalkyl trimethylsilyl ethers, generally, in reasonable to good yield. When bis(chlorodimethylsilyl)ethane or 1,5-dichlorohexamethyltrisiloxane is used instead, the corresponding cyclic silylalkyl silyl ether is formed in moderate to good yield (eq 82). ... 

Bis (3-carboxypropionyl) peroxide. See Succinic acid peroxide Bis (p-chlorobenzoyl) peroxide. See p,p -Dichlorobenzoyl peroxide 1,3-Bis (chlorocarbonyl) benzene. See Isophthaloyl dichloride 1,2-Bis (chlorodimethylsilyl) ethane. See... 

Tetramethyldichlorodisilethylene CAS 13528-93-3 EINECS/ELINCS 236-871-0 Synonyms 1,2-Bis (chlorodimethylsilyl) ethane ... 

Formation of Organozinc Carbenoids. When aromatic aldehydes and certain , -unsaturated carbonyl compounds are treated with zinc and l,2-bis(chlorodimethylsilyl)ethane, an organozinc carbenoid results. This two-electron process is postulated to occur as depicted in eq 8. Sequential reaction of the two silicon atoms with the zinc carbonyl complex and subsequent extrasion of the cyclic siloxane (23) gives rise to the putative organozinc carbenoid... 

Bis(trimethylsilyl)acetamide. Bis(trimethylsilyl)acetamide (BSA) has been formulated as iV,iV-bis(trimethylsilyl)acetamide as well as the imidate form. The NMR spectra of a number of silylamide derivatives ( C, Si, and 0) have been investigated. Whereas BSA is seen to exist in the imidate form, some analogs, for example bis(trimethylsilyl)formamide, exist in the IVW-bis(trimethylsilyl) form, and the product obtained by the interaction of l,2-bis(chlorodimethylsilyl)ethane with BSA is also clearly in the alternative foim Trimethylsilyl derivatives of hydroxamic acids are formed in reactions using hexamethyl-disilazane and are similar in structure to BSA. This entry will concentrate on examples from the more recent literature. 

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