DD294027A5 - PROCESS FOR PREPARING SILICLE-CONTAINING DICYCLOPENTADIEN DERIVATIVES - Google Patents

Abstract

The invention relates to a process for the preparation of silicon-containing dicyclopentadiene derivatives, which are widely applicable as intermediates in organic synthetic chemistry. The object of providing a process for preparing silicon-containing dicyclopentadiene derivatives which selectively allows the incorporation of silicon-containing groups into the furan ring under mild reaction conditions is achieved according to the invention by the cyclopentadiene derivatives substituted on the norbornene ring with H-silanes or H-polysiloxanes in a molar ratio of Si-H units to double bonds of 1:10 to 10: 1 in the presence of a hydrosilylation catalyst in a concentration of 10 1 to 10 5 mol / mol double bond at a reaction temperature of 298 to 423 K. {Dicyclopentadiene; H-silane; H-siloxane; hydrosilylation; hydrosilylation}

Description

For this 22 pages formulas

Field of application of the invention

The invention relates to eir. Process for the preparation of silicon-containing Dicyclopentadienderivate that are widely applicable as intermediates in organic synthesis chemistry.

4 294 Characteristics of the known state of the art

It is known (AI NOGAIDELI, Soob, Akad., Nauk, Gmiln, SSR, Org., Kh., 66, No. 3 (1972) 601; 82 (1976) 089-502) that hydrosilylation of olec- cyclopentenols on the double bond of remains Norbornenrlngos boechrilnkt Only dio application drastic Reaktinnsbedlngungon -. Roaktlonstomporaturon of 160 to 200 ⁰ C, Roaktlonszolton of 60 to 70 hours at Halosilanaddition Norbornonring, using dor roaktivsten silanes - yumgt ever Oino hydrosilation on the Furanringdoppelbindung (SU 767112),

The only feasible route to the hydrosilylation and functionalization of dicyclopentadione is given in DE 3632 792 dio hydrosilylation of Norbornenringtioppelblndung followed by hydroformylation dor Furanrlngdoppolbindiing.

It is further known (US Pat. Nos. 2,385,768,239,4682,2389136,2375767,2375768,2382038,2400873,2395452, 2383608,2393610,2385787,3230202) that the reaction of the dicyclopentadiene with H-acid precursors leads only to a very wide range of alkyl halide , Alcohol, ether, sulfide and amide compounds, with no reaction taking place on furan ring double bond. For the selective conversion of the furan ring double bond, only the phase-transfer-catalyzed addition of a bihalocarbene unit has hitherto been known (Tetrahodron Letteis No. 49 (1964) p.3745-3749).

Object of the invention

The invention has a method of producing silicon-containing dicyclopentadiene derivatives for the ziol, which allows incorporation of various siliceous groups into the furan ring.

Explanation of the essence of the invention

The object of the invention is to provide a process for the preparation of silicon-containing dicyclopentadione derivatives which selectively gassattot the incorporation of silicon-containing groups into the donor ring under mild reaction conditions.

The object is achieved in that

Cyclopentadiene derivatives of the general formulas I to V ₁ in which

Y: a halogen, preferably chlorine or bromine, an -OR), an -OOC-R7-, an-SRj or -NHCO-R4 group and Z: an -O-Rr-O or an -OOC- Rff COO group symbolizes

R, = H, a straight-chain, branched-chain or cyclic alkyl, an aryl, an alkylaryl, a mono- or polyhaloaryl,

haloalkyl, hydroxyalkyl or halohydroxyalkyl, an alkylpolyalkoxy, an alkylarylpolyalkoxy,

Haloalkylpolyalkoxy- or a polyalkoxy radical, R ₂ = H, a halogen, a straight-chain, branched-chain or cyclic alkyl, an aryl, a mono- or polyhaloalkyl ·

or hydroxyalkyl, an alkyl, mono or polyhydroxyalkyl or alkoxyalkyl ester of the Strukturon-OOC-Rj-COO-ReOder-OOC-Rj-COO-R;

R] / R ₄ = a straight-chain, branched-chain or cyclic alkyl or an aryl radical, Rj / R »= a straight-chain, branched-chain or cyclic alkyl radical or a single bond, Re = a straight-chain, branched-chain or cyclic alkyl, a mono- or polyalkoxy or hydroxyalkyl,

R ₇ = an alkyl mono or alkyl polyalkoxy, an alkylaryl mono- or polyalkoxy or a haloalkyl mono- or

Polyalkoxy radical and R ₈ = a straight-chain, branched-chain or cyclic alkyl, a mono or polyhaloalkyl, -hydroxyalkyl or

halohydroxyalkyl, an alkylpolyalkoxy, an alkylarylpolyalkoxy or an oxyalkoxy radical,

with M-silanes of the general formula VI, in the Xi, X ₂ and X _{3 is} a halogen, preferably chlorine, an alkyl radical having up to 18 C atoms, preferably a methyl or ethyl radical, an aryl radical, preferably a phenyl radical, or a Alkoxy, preferably a methoxy or ethoxy, symbolize, or H-siloxanes of the general formula VII to IX, in which X ₄ and X ₄ = alkyl or aryl radicals, preferably methyl, ethyl or phenyl radicals, X ₆ = an alkyl or aryl radical, preferably a methyl, an ethyl or a phenyl radical, oaer one

Trisalkylsiloxanylrest, preferably a Trimethyisiloxanylrest (at m = 0), X ₇ = hydrogen and

X ₈ = hydrogen, a halogen, preferably chlorine, an alkoxy, alkyl or aryl radical, preferably a methoxy,

an ethoxy, a methyl, an ethyl or phenyl radical, and η = 1 to 200, preferably Ibis 50, in particular 1 to 20, especially 1 to 8,

m = 0 to 199, preferably 0 to 49, in particular 0 to 19, especially 0 to 5, especially 0,

η + m = 1 to 200, especially Ibis 100, especially 1 to 40, especially 1 to 18, especially 5 to 8, q = 1 to 200, preferably 1 to 20, in particular 1 to 10, especially 1 to 5, very specifically 1 to 3,

r = 1 to 20, preferably Ibis 10, in particular Ibis 8, especially 4,

s = 0 to 19, preferably 0 to 9, in particular 0 to 8, especially 0,

r + s = 4 to 20, preferably 4 to 10, especially 4 to 8 _< especially 4, are> 0

- = - to 19, preferably - to 9, s i9 y

in particular - to 8, especially - to 4, 8 4

in a molar ratio of Si-H units to double bonds of 1:10 to 10: 1 in the presence of a hydrosilylation catalyst in a concentration of 10 " ¹ to 10 ~ ⁶ mol / mol double bond at a reaction temperature of 298 to 423K.

The process according to the invention is characterized by the fact that without problems under ointnch runlisiorbiiron Roaktinnsbohn the Si-C bond at Fiirnnrlny this broiton Pfllotto of Dicyclopontndiondorivnton golinut. This is quite surprising since the hydrosilation of the furan ring doubling bishor not or only in wonigon Exceptions with great difficulty under species rounging the chlorosilano hol holior temperature and oxtrom

long reaction times succeeded,

From the broiton pad of Cyclopontndiondorivato dor allgomoinon Formoln I and Il wordon boborzugt Vorbindunyon

used in which

Ri »a goradkottigor, a prime chain cyclic alkyl rust with 1 to 20 C atomon, oon phonyl odor nnphlhylrost,

an alkylphenyl radical having 1 to 20 C-atomone in the alkyl group, in the form of mono-orodine polyclilorononitrile, or in monodoro

Polychloro, -lluor-, -Bromo- or -hydroxyalkylrest with 2 to 20 C-Atomon, oin mono-odor polychlorine resp.

Bromhydroxyalkylrest with 3 to 20 C-atoms I. '. 'Or alkyl group, an alkyl, oin alkylphonyl, oin alkylnaphthyl odorein Haloalkylpolyethoxy- or -polypropoxyrest n.'t up to 200 ethylene odor Propylonoxidoinhoiton and 1 to 20 carbon atoms in the alkyl group or a Polyethoxy- l> iw. -propoxyrost up to 200 ethylene odor

Propylene oxide, R: "a straight-chain, branched-chain or cyclic Alkylrnst with 1 to 20 C atomon, oln Phonyl odor Nnphthylrost

or a mono- or polyfluoro, -bromo-, -chloro- or -hydroxyalkyl radical having 1 to 20 C-atom, R3 / R4 "is a straight-chain, branched or cyclic alkyl radical having 1 to 20 C atoms, a phenyl-odor oin

Naphthylrestund Rj "is a straight-chain, branched-chain or cyclic alkyl radical having 1 to 20 C atoms.

Of the wide range of cyclopentadione derivatives of the general formulas Hf to V, preference is given to using compounds in which Rj "is a straight-chain, branched-chain or cyclic alkyl radical having 1 to 20 C atomon, a mono-odor

Polyhydroxyalkyl radical having 1 to 20 C atoms or a polyethoxy or -propoxyrost up to 200 Ethylon odor

Propylene oxide units, R; an alkyl, an alkylphenyl, an alkylnaphthyl or a haloalkylpolyethoxy or -po.ypropoxyrostone with up to

200 ethylene or propylene oxide units and 1 to 20 carbon atoms in the alkyl group, R i = a straight-chain, branched-chain or cyclic alkyl radical having 1 to 20 C atomon, a mono-odor polychloro,

fluoro or hydroxyalkyl radical having 2 to 20 C atoms, a mono- or polychloro or -bromhydroxyalkylrost having 3 to 20 C atoms in the alkyl group, or a polyothoxy or propoxy radical up to 200 ethylene or

Propylene oxide units and Rg = a straight-chain, branched-chain or cyclic alkyl radical having 1 to 20 C atoms.

Particularly suitable compounds of the cyclopontadiene derivatives of the general formulas I to V are those in which the alkyl radicals are: methyl, ethyl, isopropyl, isobutyl, cyclohexyl, dodecyl, palmityl or stearyl radicals, alkylaryl radicals: ethylphenyl or C. - to C, ₂ alkylphenyl, Chlorarylreste: monochloro- or Pentachlorphenylreste Chloralkylreste: 2-chloroethyl, 1,3 or 2,3-· Dichlorpropylreste, hydroxyalkyl radicals: · hydroxyethyl or -propylreste,

Chloro, bromo or fluoroalkyl radicals: -CH ₂ Cl, -CHCl ₂ , -CCl ₃ , -CHjF, -CHF ₂ , -CF ₃ , -CH ₂ , -CH ₂ Br, -CHBr ₂ , -CBr ₃ , - CH ₂ (CF ₂ ) ₂ H, -CH ₂ (CF ₂ ) ₄ H, -CH ₂ (CF ₂ ) _e H, -CH ₂ (CF ₂ I ₁ H, -CHj (CF ₂ I ₁₀ H, -CHj (CF ₂ ) "H, -CHj (CF ₂ J ₁₄ H, -CH ₂ (CF ₂ ) _ie H, -CH ₂ (CF ₂ I ₁₁ H, -CH ₂ (CF ₂ ) _N H, -CH ₂ ( CF ₂ ) ₂₂ H, and the

Alkoxy-containing radicals of the variables R ₁ to R ₉ : -CH ₂ CH ₂ OCH ₂ CHjCl or "CHjCHjOCHjCH ₂ OCH ₂ CH _3. Of the H-silanes are particularly suitable trichlorosilane, methyldichlorosilane, dimethylchlorosilane, triethoxysilane, methyldiethoxysilane and dimethylethoxysilane.

From the group of H-siloxanes, for example, compounds such as pentamethyldisiloxane (MM "), heptamethyltrisiloxane (M ₂ D ^H or MDH ^H ) or nonamethyltetrasiloxane (M ₃ T") can be used.

The reaction of the reactants proceeds successfully in the temperature range mentioned. In general, the reaction is carried out in the temperature range of 333 to 423K. A particularly favorable course of the process can be observed at reaction temperatures of 353 to 423K. A particularly high reaction rate occurs at 373 to 423 K, the optimum being in the temperature range from 403 to 423K.

Of the known hydrosilylation catalysts, preference is given to complex compounds of the elements of the fl. Transition group, eg. As of Co, Ni, Ru, Rh, Pd or Pt used. Of particular interest are the platinum-based hydrosilylation catalysts η, of which, in particular, hexachloroplatinic acid, which is said to derive from it by modification with vinylsiloxanes producible halide-free organoplatinum species and catalyst systems, as described in US-PS 3220972, should be mentioned. The catalyst concentration is between 10 ^"1 and 10 ~ ⁶ mol / mol of double bond. Preferably, to be concentrations of 10 ^-2 to 10 ^-4 mol / mol of double bond used as a particularly favorable have catalyst levels of 5 10 ~ ³ to 5 10." ⁴ mol / mol double bond proved.

In the reaction of hydroxyl-containing dicyclopentadiene derivatives, it may be appropriate to carry out the reaction in the presence of a solvent, such as toluene.

The reaction time depends essentially on the reaction temperature, the type and concentration of the catalyst and the H-silanes or H-siloxanes to be reacted with each other and the dicyclopentadiene derivatives, and can easily be determined for each reaction system by gas chromatography or IR spectroscopy. The use of the highly reactive chlorine-containing H-silanes and catalyst concentrations and reaction temperatures lying at the upper limit of the stated range have a reaction-shortening effect.

The process according to the invention makes it possible, for example, to prepare novel dicyclopentane derivatives substituted on the furanp.ig of the general formulas X to XXXIX and 1 to 22, in which the symbols have the abovementioned meaning.

AutfuhrungtbttpUl ·

B "l" p4tl1

1.02 g of 8-, 9-methoxytrlcyclo | 5.2, 1.0 ^M | d6c-3-ene, 2.7 g of homonothioltrellosin (M) O ") and 0.19 ml of 0.1 η H ₂ PtCl 6 .6 M ₁ O in Isopropanol was premixed at room temperature by stirring with solvent.Alone Ronktlonszoite of 30 hours of a reaction torque of 403K is dehydrated in vacuo to give 1.6 g of Ronction product, which is a boiling bract of 388 to 400K (at 10GPa) and following Structure and Cliniccticism mifwolst:

IR: Ooppelbindungsband bei 3030cm 'no longer detectable ¹ H-NMM: - at 0.04ppm signal dor-Si (CH,) j-group

- at O.O to -0 06ppm signals of the protons of the «SiCHj group ¹³ C-NMR: - at 1.81 ppn, 'for the C atom of the -SifCHsl group

- at - 1.41 pp il for the C atoms of the «SiCHj group

Example 2

2.7 g of 8-, 9-chloroacetic acid ester of tricyclo | 5.2.1.0 ") dec-3-ene, 5.55 ml of M ₂ D" and 0.375 ml of 0.1 η H) PtClg-6H; O in isopropanol are mixed together at room temperature by stirring. After a reaction time of 38 hours at a reaction temperature of 408K, the reaction mixture is distilled in vacuo. There are 2.2 g of reaction product or 'old', which has a boiling range of 413 to 423K (26Pa) and the following structure and characteristics:

Ct C

IR: very weak band at 3030 cm " ¹ shows residues of the chloroacetic acid ester on 'H-NMR: at 0.06 ppm signal of the Si (CH) group

at 0.02 to -0.06 ppm signals of the protons of BSiCH ₃ -GrUpPe ³ C-NMR: at 1.64 ppm for the C-atom of the -Si (CH ₃ ) ₃ group

at -1.55 ppm signal for the C atoms of the eSiCH ₃ group

Example 3

1.74 g of 8-, 9-Betachlorethoxyethanolether of tricyclol5,2,1,0 "dec-3-ene, 4,25ml M ₂ D" and 0,2ml 0,1 η H ₂ PtCl ₆ 6H ₂ O in isopropanol mixed together at room temperature by stirring. After a reaction time of 36 hours at a reaction temperature of 408K, the reaction mixture is distilled in vacuo. There are obtained 1.8 g of crude product which has a boiling range of 413 to 428 K (39.6 Pa) and the following structure and characteristics:

IR: no double bond band at 3030cm ' ¹ detectable' H-NMR: - beiO, O6blsO, O4ppmSignalder-S! (CH ₃ ) ₃ -group

- at -0.02 to -0.04 ppm signals of the protons of the «SiCH ₃ group ¹³ C-NMR: - ppm ppm signal for the C atomic ladder-SilCHsM group

- at -1.21 ppm signal for the C atoms of the eSiCH _} group

Example 4

3.11 g of 8-, 9-bromotricyclo | 5.2.2.0 ² ') dec-3-ene, 6.78 ml of M _a D ^H and 0.432 ml of 0.1 η HjPtCl ₈ · 6H ₂ O in isopropanol premixed at room temperature by stirring. After a reaction time of 3 hours at a reaction time of 403 K, the reaction mixture is distilled in vacuo. There are obtained 1.73 g of reaction product having a Siodoboreich of 388 to 403K (20Pa) and the following structure and characteristics:

IR: no double bond band at 3030cm ' ¹ detectable' H-NMR: - at 0.04ppm signal of the -Si (CH ₃ ) ₃ group

- at 0.02 to -0.04 ppm signals of the protons of the "SiCHj group" ³ C-NMR: - at 1.77 ppm signal for the C atoms of the -Si (CH ₃ ) ₃ group

- at -1.61 ppm signal for the C atoms of the

example

2.23 g of 8-, 9-ethoxy-ethoxyethanol ether of tricyclo-Lö ^ .i.

5.2 ml of M] D ^H and 0.252 ml of 0.1 η H] PtCl ₄ 6H] O in isopropanol are mixed together at room temperature by stirring. After a reaction time of 17 hours at a reaction temperature of 408K, the reaction mixture is distilled in vacuo. There are obtained 2.95 g of reaction product having a boiling range of 423 to 442 K (20 Pa) and the following structure and characteristics:

C HjC H ₁ O (CH ₁ CH ₁ O-

IR: no double bond band at 3030cm " ¹ detectable ¹ H-NMR: - beiO, C4ppmSlgnalder-Si (CHj), - Griippe

- At 0 to -Ο, Οβρρπι signals of the protons of the "SiCHj group" C-NMR: - beii ^ ppmSignalfür the C atom of the SKCHjlj group

at -i ^ oppmu signal for the C-atom of the "SiCH ₃ group

Examples

2.53 g of 8-, 9-triethylene glycol ether of the tricyclo | 5.2, 1, 0 "| 3-ens,

Si (CH, y

4.17 ml of M ₂ D "and 0.27 ml of 0.1 η H ₁ PtCl ₉ · 6H ₂ O in isopropanol are mixed together by stirring at room temperature After a reaction time of 35 hours at a reaction temperature of 408K, the reaction mixture is distilled in vacuo. There are obtained 2.62 g of reaction product having a boiling range of 428 to 447 K (20 Pa) and the following structure and characteristics:

IR: very weak band at 3030cm " ¹ shows residues of triethylene glycol ether on ' ³ C-NMR: - at 1.35 ppm signal for the C atoms of the -Si (CH ₃ ) ₃ group - at -4.07 ppm signal for the C atoms of the »SiCHj group

Example 7

1.48 g 8-, 9-Chlor6ssigsäureester of tricyclo [5,2,1,0 ^{2 'a} | dec-3-ene, 1.22 g Siiiconöl with a statistical composition of (CH3) 3 Si [OSi (CH3) ₂ l _l |, _e (OSiHCH _] ) ₁ } _{> l} OSi (CH ₎ ) 3 and 0.195 ml of 0.1 η H ₂ PtCl ₆ 6H ₂ O in isopropanol are mixed together at room temperature by very vigorous stirring. After a reaction time of 48 hours at a reaction temperature of 40SK, the reaction mixture is distilled in vacuo. After distilling off all the constituents boiling to a temperature of 383 K (26.4 Pa), a viscous product is obtained which has the following characteristics:

IR: ¹ H-NMR:

weak bands at 3030 and 1660 cm ^-1 indicate small residues of the chloroacetic acid ester

- very weak band at 2160cm " ¹ indicates remaining Si-H groups

between 0.1 and 0.4 ppm signal of the = Si (CH ₃ ) j group and the eSiCHj groups

- Signals for the protons at the double bonds are not detectable.

- 40

? 9 4 O 2 7

/ χ * O I * O ⁵ sl S i f χ " H

0 4 0 2

Χ <τ ~ "*

ϊ "

ι X

szie

-1b '

"rV

XIX

fr ;

XXIII

(\) ₃ s · 7 ° V Γ ⁸ I ¹ '

O Si

3 5CXi

'm

^s i

ο s'i b

sl

P ⁵ '

-41,

^ XVIII

(X, I ₅ Si

J] L

s ί (χ J

ι Xf ι

ι *

Si O

S ₍ i

S ₁ ; ο

-if

4027

) j

(X _1. ) S i

XX X Ij

(X ₁₁ ) Si

S i (X ₁ ,),

MXS

S i (X J

Si O

XXXIV

ο β.

K)

J * r O Si O < S, i K U 3

OS _f i

Si O ι

Si O I

Χχχνί \

-JH

2 9 4 0 2

S, l O

S i O

Si OSi (X _{1 +} J ₁

XXXlX

Si O

Si O X.S i

Si O

Si O

• (χ «Λ * β

L-Si O

.. ⁶

Si O

r-Si O

X.

Si O

Υ «S ₁ . ο

χ "

Si O

-lh 2 9 .4 O 2 7

w 1 ι ν. J χ * X, ι o ^L S ₍ i O S ₍ i O if X ₆ /

s i

i o

χ *

sji ο

i o

x *

S, i O

S ₁ , 0 Χ

Υ "

* 'Q

Si O

SiO> Si (Xj ₂

-21-

^L Si O

SiOSi (X ₁ ^ X,

-Si 0

Si O

AQ

2940

 Si O

ή ο / is

fr \ Si O

Ο + ¹

Si

ι 04-1 X4.

 IV

το

Si O

ZA

⁵ • s'i Ο ι S , > Γ

Claims (25)

1. Ancestors for the preparation of silicon-containing dicyclopontadione dorivato, characterized in that cyclopentadiene derivatives of general formula I to V in which Y: a halogeno, oino-ORi, oine-OOC-R2-, mono-SRy- or mono-NHCO-R ₄ - Gruppo and Z: symbolizes a -O-Re-O or an -OOC-Rr-COO-nruppo, Rv = H, a straight-chain, branched-chain or cyclic alkyl, an aryl, an alkylaryl, a mono- or polyhaloaryl, -haloalkyl, -hydroxyalkyl or halohydroxyalkyl, an alkylpolyalkoxy, an alkylarylpolyalkoxy, a halo ' kylpolyalkoxy- or a polyalkoxy,
R ₂ = H, a halogen, a straight-chain, branched-chain or cyclic alkyl, an aryl, a mono- or polyhaloalkyl or -hydroxyalkyl radical, an alkyl, mono- or polyhydroxyalkyl or -alkoxyalkyl ester of the structures -OCO-R ₅ -COO-R ₀ or -OOC-R ₆ -COO-R ₇ , R3 / R4 = a straight-chain, branched-chain or cyclic alkyl or an aryl radical, R _B / R ₃ - a straight-chain, branched-chain or cyclic alkyl radical or a Single bond,
R ₆ = a straight-chain, branched-chain or cyclic alkyl, a mono- or Polyalkoxy or hydroxyalkyl radical,
R ₇ = an alkyl mono or alkyl polyalkoxy, an alkylaryl mono- or polyalkoxy- or a Haloalkylmono- or -polyalkoxy and
R ₈ = a straight-chain, branched-chain or cyclic alkyl, a mono or Polyhaloalkyl, hydroxyalkyl or halohydroxyalkyl, an alkylpolyalkoxy, an alkylarylpolyalkoxy or a polyalkoxy radical, with H-silanes of the general formula VI in which X _1, X ₂ and X ₃ is a halogen, an alkyl group having up to 18 carbon atoms, an aryl radical or an alkoxy radical, symbolize, or H-siloxanes of the general formulas VII to IX in which X ₄ and X ₆ = alkyl or aryl radicals, X ₅ = an alkyl or aryl radical, or a trisalkylsiloxanyl radical, X ₇ = hydrogen and X ₈ = hydrogen, a halogen, an alkoxy, alkyl or aryl radical, represent and η = 1 to 200, m = 0 to 199, η + m = 1 to 200, q = 1 to 200, r = 1 to 20, s = 0 to 19, r + s = to 20, and for> 0 γ = - ^ - until 19ist, be reacted in a molar ratio of Si-H units to double bonds of 1:10 to 10: 1 in the presence of a hydrosilylation catalyst in a concentration of 1O ^-1 to 10 ~ ⁵ mol / mol double bond at a reaction temperature of 298 to 423 K. 2. A process for preparing silicon-containing Dicyclopentadienderivate according to claim 1, characterized in that are used by the cyclopentadiene derivatives of the general formulas I and II compounds in which R ₁ = straight chain branched chain or alkyl radical having from 1 to 20 carbon atoms, a phenyl or naphthyl radical, an alkylphenyl radical having 1 to 20 C atoms in the alkyl group, a mono- or polychlorophenyl radical, a mono- or polychloro, fluoro, bromo or hydroxyalkyl radical having 2 to 20 C atoms, a mono- or polychloro or bromo-hydroxyalkyl radical having 3 to 20 C atoms in the alkyl group, an alkyl, an alkylphenyl, an alkylnaphthyl or a haloalkylpolyethoxy or -polypropoxy radical having up to 200 ethylene or propylene oxide units and 1 to 20 C atoms in the alkyl group or a polyethoxy or -propoxy radical with up to 200 ethylene or propylene oxide units, R ₂ = a straight-chain, branched-chain or cyclic alkyl radical having 1 to 20 C atoms, a phenyl or naphthyl radical or a mono- or polyfluoro, bromo, chloro or hydroxyalkyl radical having 1 to 20 C atoms, R3 / R4 = a straight-chain, branched-chain or cyclic alkyl radical having 1 to 20 C atoms, a phenyl or a naphthyl radical and R ₅ = a straight chain, branched chain or cyclic alkyl radical having up to 20 carbon atoms is. 3. A process for preparing siliciumhaltigor dicyclopentadiene derivatives according to claim 1, characterized in that of the cyclopentadiene derivatives of general formulas III to V compounds are used, in which Re = branched chain branched chain geranium cyclic alkyl radical having up to 20 carbon atoms, a mono- or polyhydroxyalkyl radical having 1 to 20 C atoms or a polyethoxy or -propoxy radical up to 200 ethylene or propylene oxide inositols, R ₇ = an alkyl, an alkylphenyl, an alkylnaphthyl or a haloalkylpolyethoxy or polypropoxy with up to 200 ethylene or propylene oxide units and 1 to 20 carbon atoms in the alkyl group Re = branched chain branched or cyclic alkyl radical having up to 20 carbon atoms, a mono- or polychloro, fluoro or hydroxyalkyl radical having 2 to 20 C atoms, a mono- or polychloro or bromohydroxyalkyl radical having 3 to 20 C atoms in the alkyl group, or a polyethoxy or -propoxy radical with up to 200 ethylene or propylene oxide units and R ₉ = a geradkettiger.zwezweigtkettiger or cyclic alkyl radical having 1 to 20 carbon atoms is. 4. A process for the preparation of silicon-containing Dicyclopentadierrderivate according to claim 1 to 3, characterized in that of the cyclopentadiene derivatives of the general formula I to V compounds are used in which the Alkyl radicals: methyl, ethyl, isopropyl, isobutyl, cyclohexyl, dodecyl, palmityl or stearyl radicals, Alkylaryl radicals: ethylphenyl or C ₇ - to C ₁₂ -alkylphenyl radicals, chloroaryl radicals: monochloro- or pentachlorophenyl radicals chloroalkyl radicals: 2-chloroethyl, 1,3- or 2,3-dichloropropyl radicals, hydroxyalkyl radicals: hydroxyethyl or -propyl radicals, Chloro, bromo or fluoroalkyl radicals: -CH ₂ Cl, -CHCl ₂ , -CCl ₃ , -CH ₂ F, -CHF ₂ , -CF ₃ , -CH ₂ , -CH ₂ Br, -CHBr ₂ , -CBr ₃ , -CH ₂ (CF ₂ I ₂ H, -CH ₂ (CF ₂ I ₄ H, -CH ₂ (CF ₂ I ₆ H, -CH ₂ (CF ₂ I ₈ H, -CH ₂ (CF ₂ I ₁₀ H , -CH ₂ (CF ₂ I ₁₂ H, -CH ₂ (CF ₂ I ₁₄ H, -CH ₂ (CF ₂ I ₁₆ H, -CH ₂ (CF ₂ I ₁₈ H, -CH ₂ (CF ₂ I ₂₀ H , -CH ₂ (CF ₂ I ₂₂ H, and the alkoxy-containing radicals of the variables R ₁ to Rg: -CH ₂ CH ₂ OCH ₂ CH ₂ Cl or -CH ₂ CH ₂ OCH ₂ CH ₂ OCH ₂ Ch ₃ are. 5. The method according to claim 1, characterized in that are used as H-silanes compounds of general formula VI, in which X ₁ , X ₂ and X _{3 is} a halogen, an alkyl radical having up to 18 carbon atoms, an aryl radical or symbolize an alkoxy radical. 6. The method according to claim 1 and 5, characterized in that H-silanes of the general formula VI are used in which X ₁ , X ₂ and X _{3 is} chlorine, a methyl, an ethyl, a phenyl, a methoxy or symbolize ethoxy. 7. The method according to claim 1,5 and 6, characterized in that are used as H-silanes of the general formula VI Trichlorosilane, methyldichlorosilane, dimethylchlorosilane, triethoxysilane, methyldiethoxysilane or dimethylethoxysilane. 8. The method according to claim 1, characterized in that are used as straight-chain, branched-chain or cyclic H-siloxanes or H-polysiloxanes compounds of the general structural formulas VII to IX in which X ₄ and X ₆ = alkyl or aryl rust, X5 = an alkyl, an aryl or a trisalkylsiloxanyl radical, X ₇ = hydrogen and X ₈ = hydrogen, a halogen, an alkoxy, alkyl or aryl radical, represent and η = 1 to 200, m = 0 to 199, η + m = 1 to 200, q = 1 to 200, r = 1 to 20, s = 0 to 19, r + s = bis20and for> 0 - = ^ -bis19.
s 1 y 9. The method according to claim 1 and 8, characterized in that straight-chain, branched-chain or cyclic H-siloxanes or H-polysiloxanes compounds of the general structural formulas VII to IX are used, in which X ₄ and X ₆ = methyl, ethyl or phenyl radicals, X ₅ = a methyl, an ethyl, a phenyl or a trimethylsiloxanyl (at m = 0),
X ₈ = hydrogen, chlorine, a methoxy, an ethoxy, a methyl, an ethyl or phenyl. 10. The method according to claim 1 and 8, characterized in that are used as goradkottige or branched chain H-siloxanes compounds of the general structural formulas VII or VIII, in which η = 1 to 50, m = 0 to 49, η + m = 1 to 100 and q = 1 to 20. 11. The method according to claim 1,8 and 10, characterized in that as goradkottigo odor branched chain H-siloxanes compounds of the general structural formulas VII or VIII are used, in which η - 1 to 20, m = 0 to 49, η + m = 1 to 100 and q = 1 to 20. 12. Process according to Claims 1, 8, 10 and 11, characterized in that the straight-chain or branched H-siloxanes used are preferably compounds of the general structural formulas VII or VIII in which = 1 to 8, m = 0 to 19, n + m = 1 bis40undq = 1 to 10. 13. The method of claim 1,8 and 10 to 12, characterized in that are used as straight-chain or branched-chain H-siloxanes in particular compounds of the general structural formulas VII or VIII, in which m = 0 to 5, especially 0, η + m = 1 to 18, especially 5 to 8 and q = 1 to 5, especially 1 to 3, is. 14. The method of claim 1,8 and 10 to 13, characterized in that as straight-chain or branched-chain H-siloxanes of the general structural formulas VII or VIII specifically pentamethyldisiloxane (MM ^H ), heptamethyltrisiloxane (M ₂ D "odor MDH ^H ) odor Nonamethyltetrasiloxan ( MaT ") are used. 15. The method according to claim 1 and 8, characterized in that as cyclic H-siloxanes, preferably compounds of the general structural formula IXeingosetztwerdon, indonitrile = 1 to 10, s = 0 to 9, r + s = 4 to 10, and for> 0 = 4 "to 9 is. s y 16. The method according to claim 1,8 and 15, characterized in that are used as c \ clische H-siloxanes in particular compounds of the general structural formula IX, in which r = 1 to 8, s = 0 to 8, r + s = 4bis8und- = 4th - is up to 3. S o 17. The method according to claim 1,8,15 and 16, characterized in that are used as cyclic H-siloxanes compounds of the general structural formula IX, in which specifically r = 4, s = 0, r + s = 4, and für> 0 γ = - ^ - bis4ist. 18. The method according to claim 1, characterized in that preferably a reaction temperature of 333 to 423 K is applied. 19. The method according to claim 1 and 18, characterized in that the reaction temperature is in particular 373 to 423 K. 20. The method according to claim 1,18 and 19, characterized in that the reaction temperature is specifically 403 to 423K. 21. The method according to claim 1, characterized in that as hydrosilylation preferably complex compounds of the elements of the 8th subgroup, z. As the Co, Ni, Ru, Rh, Pd or Pt, in a concentration of 10 ~ ² to 10 ~ ⁴ mol / mol double bond. 22. The method according to claim 1 and 21, characterized in that the catalyst concentration preferably 5 × 10 ^-3 to 5 × 10 ^-4 mol / mol of double bond is. 23. The method according to claim 1, characterized in that the molar ratio of double bonds to Si-H bonds is preferably between 3: 1 and 1: 3. 24. The method according to claim 1 and 23, characterized in that the molar ratio of double bonds to Si-H bonds in particular between 1.2: 1 and 1: 1.2. 25. A process for the preparation of silicon-containing Dicyclopentadienderivate, characterized in that cyclopentadiene derivatives of the general formulas X to XXXIX and 1 to 22 are obtained, in which the symbols have the meaning given.