78907-64-9

Upstream product

• 78907-52-5 C₁₅H₂₉LiSSi₃ 
• 29955-10-0 dibromobis(trimethylsilyl)methane 
• 930-69-8 sodium thiophenolate 
• 62139-74-6 Brom(bromdimethylsilyl)bis(trimethylsilyl)methan 
• 80431-36-3 2,2-Dimethyl-4,4-diphenyl-1,3,3-tris(trimethylsilyl)-1-aza-2-silacyclobutan 
• 108-98-5 thiophenol 
• 78907-42-3 Brombis(trimethylsilyl)methan 
• 78907-46-7 Brom(dimethylphenylsilyl)bis(trimethylsilyl)methan 

Relevant academic research and scientific papers

Reactivity of the Labile Silaethene Me2Si=C(SiMe3)2, Stored as Ph2C=NSiMe3 Adducts

Silaethene Me2Si=C(SiMe3)2 (1), stored as Ph2C=NSiMe3 adducts and regenerated from the adducts at about 100 deg C as a reaction intermediate, combines with reactants a-b (e.g.HO-H, RO-H, RCOO-H, RS-H, RHN-H, Ph2CN-H, RO-SiR3, R2N-SiR3, Ph2CN-SiR3, Cl-GeR3, Cl-SnR3) with insertion into the a-b bond, with a=b (e.g.O=CPh2, Me3SiN=CPh2, CH2=CHOMe, cis-piperylene), a=b=c (e.g.RN=N=N, O=N=N), a=b-c=d (e.g. butadiene, isoprene, trans-piperylene, 2,3-dimethylbutadiene, cyclopentadiene, anthracene, benzophenone, N-trimethylsilylbenzophenoneimine) under -, - as well as -c ycloaddition and with a=b-c-H (e.g. propene, butenes, isoprene, 2,3-dimethylbutadiene, acetone) under ene reaction.According to relative reaction rates, insertion and -cycloadditions seem to proceed in two reaction steps, whereas -cycloadditions and ene reactions with organic dienes and enes obviously are one step reactions.For reactivities cf.Table I. - Key words: Silaethene Me2Si=C(SiMe3)2, Insertions, Cycloadditions, Relative Reactivities

On the Way to Silaethene Me2Si=C(SiMe3)2: Trisilylated Methanes (Me3Si)2(Me2XSi)CY (X=e. g. Hal, RO, RS; Y e. g. Br, Li)

Bromotrisilylmethanes (Me3Si)2(Me2XSi)CBr (1 - 15) are formed as a result of the reaction of (Me3Si)2(Me2PhSi)CBr (16) with iodine monochloride, bromine and iodine (X = Cl, Br, I) respectively, and also through the reaction of (Me3Si)2(Me2BrSi)CBr (1) with AgX (X = F, p-TolSO2, p-TolSO3, MesSO3, Ph2PO2, Ph2PO3, Ph2PO4) or MX (M = H, Li, Na; X = HO, RO, RS, Bu, Ph).Butyl- as well as phenyllithium convert bromotrisilylmethanes 1 - 16 at low temperatures into lithium derivatives (Me3Si)2(Me2XSi)CLi (1a - 16a).These are in some cases (X = R, RO) thermostable, whereas, in other cases they decompose more or less readily under LiX elimination and lead (in many cases via silaethene Me2Si=C(SiMe3)2) to the disilacyclobutane derivative 2 (17).Acids HZ (e. g.HCl, HOMe, Me3CBr) protonate the lithium compounds into (Me3Si)2(Me2XSi)CH as well as (Me3Si)2(Me2ZSi)CH.Butyl bromide converts the more stable lithium compounds (Me3Si)2(Me2XSi)CLi (X = R, RO, F, Ph2POn) into butyl derivatives (Me3Si)2(Me2XSi)CBu.