117984-30-2

Upstream product

• 29955-10-0 dibromobis(trimethylsilyl)methane 
• 117984-14-2 Brom(diphenylsilyl)bis(trimethylsilyl)methan 
• 117984-38-0 Diphenylsilylmethylnatrium 
• 117984-31-3 Diphenylsilylmethyllithium 
• 1631-83-0 diphenylsilyl chloride 
• 117984-10-8 Brom(bromdiphenylsilyl)bis(trimethylsilyl)methan 

Downstream Products

• 117984-19-7 (Bromdiphenylsilyl)bis(trimethylsilyl)methan 
• 117984-20-0 (Hydroxydiphenylsilyl)bis(trimethylsilyl)methan 
• 117984-34-6 (3-methyl-2-methylen-3-butenyl)diphenylsilan 
• 117984-37-9 (2,3-dimethyl-1,3-butadienyl)diphenylsilan 
• 117984-33-5 3,4-Dimethyl-1,1-diphenyl-6,6-bis(trimethylsilyl)-1-sila-3-cyclohexen 
• 117984-35-7 3-<2,2,-Diphenyl-3,3-bis(trimethylsilyl)-2-silapropyl>-4-methyl-1,1-diphenyl-6,6-bis(trimethylsilyl)-1-sila-3-cyclohexen 
• 68260-21-9 (methoxy)(diphenyl)silane 
• 117984-23-3 methyldiphenyl[bis(trimethylsilyl)methyl]silane 
• 117984-13-1 Brom(phenoxydiphenylsilyl)bis(trimethylsilyl)methan 
• 117984-21-1 (Phenoxydiphenylsilyl)bis(trimethylsilyl)methan 

Relevant academic research and scientific papers

Reactivity of the Silaethene Ph2Si=C(SiMe3)2

Silaethene Ph2Si=C(SiMe3)2 (3), generated as a reaction intermediate by the thermal elimination of LiX from Ph2SiX-CLi(SiMe3)2 (X = Br, F) or by the thermal cycloreversion of the cycloadduct of 3 and Ph2C=NSiMe3, forms adducts 3*donor, the stability of which increases in the order of donor = Et2O according to an ene reaction, with a=b (e.g.CH2=CHOMe; Ph2C=NSiMe3) or a=b=c (e.g. (t-Bu)2RSiN3, R = Me, t-Bu) or a=b-c=d with or or cycloaddition.The following order of relative reactivity of trapping reagents for Ph2Si=C(SiMe3)2 was found: Ph2CO > (t-Bu)2MeSiN3 > butadiene > 2,3-dimethylbutadiene > Ph2CNSiMe3 > (t-Bu)3SiN3 > anthracene.Summing up, it may be said that going from Me2Si=C(SiMe3)2 to Ph2Si=C(SiMe3)2 there is only a gradual but not principal change of silaethene reactivity.This change is due to increasing polarity and overcrowding of the double bond, that is increasing Lewis acidity and steric hindrance of the unsaturated silicon atom.Certainly, the former silaethene stabilizes thermally by dimerization, the latter by isomerization. - Keywords: Adduct formations, insertions, ene reactions, -, -, -cycloadditions of Ph2Si=C(SiMe3)2 ; Reactivity order of traps ; Reactivity of Me2Si=C(SiMe3)2 and Ph2Si=C(SiMe3)2

Generation and Detection of the Silaethene Ph2Si=C(SiMe3)2

Bromotrisilylmethanes (Me3Si)2(Ph2XSi)CBr (4-13; Table 1) are formed by the reaction of (Me3Si)2(Ph2HSi)CM (M = Li, Na) with bromine or with bromine/chlorine (X = H, Cl, Br) and also by treating (Me3Si)2(Ph2BrSi)CBr with KHF2 (X = F), H2O or MeOH (X = OH, OMe), MeLi (X = Me), BuLi/Br2 (X = Bu), PhLi/Br2 or PhLi/PhOLi/Br2 (X = Ph, OPh).PhLi, BuLi, and tBu3SiNa convert the bromotrisilylmethanes by Br/M exchange into compounds (Me3Si)2(Ph2XSi)CM, which may be protolyzed, alkylated, and brominated .For X = halogen the equilibrium (Me3Si)2(Ph2XSi)CM Ph2Si=C(SiMe3)2 (3) + MX exists.Thereby, silaethene 3 is formed in Et2O at -78 deg C (X/M = Br/Li) or at room temperature (X/M = F/Li, Br/Na), respectively, reversibly in low concentrations and at higher temperatures irreversibly (formation of secondary products of 3).The intermediacy of 3 has been established chemically by trapping 3 with (for example) RLi (formation of insertion products in the R-Li bond), Ph2C=NSiMe3 (formation of a cycloadduct, which may serve as a source of 3), tBu2MeSiN3 (formation of a cycloadduct), and particularly 2,3-dimethyl-1,3-butadiene (formation of Diels-Alder and ene reaction products).In the last case products and yields are independent of the origin of 3.From Me2Si=C(SiMe3)2 (1) to 3 there is only a gradual (but no principal) change of silaethene reactivity (3 is more Lewis acidic than 1). - Keywords: Silaethenes/ Bromotris(silyl)methane derivatives