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Organosilicon compounds
Silicon is just like carbon, but:
Larger
five- and six-coordinate structures positive
More electropositive
easier attack by nucleophiles
OrganoSilicon Comp
Bonds to silicon
Si-C
Si-O, Si-F
Si-Cl, Si-Br, Si-I
Si-Si
Si=Si and Si=C
OrganoSilicon Comp
Silicones !
R
Cl
Si Cl
H2O
R
HO Si OH
- H2O
R
Si O
R
- H2O
R
Si O
R
OrganoSilicon Comp
Silicones
Based on strong -Si-O- backbone
a pure -Si-Si- backbone would be weak
"Slick"
Viscosity change little with temperature
silicone oil
OrganoSilicon Comp
Ph3COCPh3
COC = 128
Ph3SiOSiPh3
SiOSi = 159
OrganoSilicon Comp
OrganoSilicon Comp
Synthesis
Direct synthesis
Si is not electropositive enough for unassisted direct synthesis
An Si/Cu alloy works better:
RCl + Si/Cu
Metathesis
SiCl4
RLi
R4Si
Hydrosilylation
HSiCl3 + R
SiCl3
OrganoSilicon Comp
Reactivity
Nucleophilic attack
Me3SiPh + F
SiMe3 H2O
H
With halogens
Si
X2
Si
X + X C
OrganoSilicon Comp
Ph4Si
Ph4Sn
Ph4Ge
Ph4Pb
OrganoSilicon Comp
Ph4Si
4-coordinate
Ph3SiF25-coordinate
Ph2Si(tropolonate)2
6-coordinate
OrganoSilicon Comp
C6(SiMe2OMe)6
OrganoSilicon Comp