| Chemical Name | Diphenylsilane |
| Synonym |
Diphenylsilane |
| CAS Number | 775-12-2 |
| EC Number | 212-271-4 |
| Beilstein Registry Number | 2935887 |
| MDL Number | MFCD00003002 |
| PubChem Substance ID | 24848906 |
| Reaxys-RN | 2935887 |
| Chemical Name Translation | 二苯基硅烷 |
| InChIKey | VDCSGNNYCFPWFK-UHFFFAOYSA-N |
| LabNetwork Molecule ID | LN00202555 |
| Canonical SMILES | C1([SiH2]C2=CC=CC=C2)=CC=CC=C1 |
| IUPAC Name | diphenylsilane |
{PUB} Crystallography Open Database (COD)|PubChem --- Multiple Silicon-Hydrogen Bond Activations at Adjacent Rhodium and Iridium Centers --- https://pubmed.ncbi.nlm.nih.gov/21077657
{PUB} Crystallography Open Database (COD)|PubChem|The Cambridge Structural Database --- Reaction of alkyne with dinickel-diphenylsilyl complexes. Preparation of an emissive disilane via consecutive Si-C and Si-Si bond-making reactions --- https://pubmed.ncbi.nlm.nih.gov/22241522
{ALF} CsF promotes the reduction of aldehydes and ketones to alcohols: J. Organomet. Chem., 148, C1 (1978); 172, 143 (1979). Esters can be reduced at elevated temperatures: Synthesis, 558 (1981). Aldehydes and ketones are also reduced in the presence of TBAF: J. Org. Chem., 53, 5415 (1988).
{ALF} In combination with an equivalent of Titanium(IV)­ isopropoxide, A13703, a mild, one-pot reduction of tertiary amides to aldehydes can be accomplished in high yield. The initial product is the enamine which can be readily hydrolyzed in situ to the aldehyde: Angew. Chem. Int. Ed., 35, 1515 (1996):
{ALF} In the presence of Tetrakis(triphenyl­phosphine)­palladium(0)­, 10548, effects the reductive cleavage of allylic acetates: J. Org. Chem., 48, 3545 (1983). With the same catalyst and a Lewis acid such as zinc chloride, ɑß-unsaturated aldehydes, ketones and esters are reduced to their saturated counterparts: J. Am. Chem. Soc., 108, 7314 (1986).
{PUB} P
{ALF} Protection of diols as diphenylsilylenes can be effected in the presence of CsF: J. Organomet. Chem., 282, 155 (1985). See Diphenyl­dichlorosilane, A12051, and Appendix 4.
{PUB} PubChe
{PUB} PubChem --- Designing the “Search Pathway” in the Development of a New Class of Highly Efficient Stereoselective Hydrosilylation Catalysts --- https://pubmed.ncbi.nlm.nih.gov/15744702
{PUB} PubChem --- Further Studies toward the Stereocontrolled Synthesis of Silicon-Containing Peptide Mimics --- https://pubmed.ncbi.nlm.nih.gov/20423092