JPH0323557B2 - - Google Patents
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- Publication number
- JPH0323557B2 JPH0323557B2 JP11905381A JP11905381A JPH0323557B2 JP H0323557 B2 JPH0323557 B2 JP H0323557B2 JP 11905381 A JP11905381 A JP 11905381A JP 11905381 A JP11905381 A JP 11905381A JP H0323557 B2 JPH0323557 B2 JP H0323557B2
- Authority
- JP
- Japan
- Prior art keywords
- phenyldisilane
- formula
- novel
- general formula
- present
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
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Description
【発明の詳細な説明】
本発明は、新規フエニルジシラン系化合物とそ
れを製造する方法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel phenyldisilane compound and a method for producing the same.
２価のケイ素中間体であるシリレンは、反応性
に富むことから特に新しい合成反応への利用が期
待され、広く研究されている。このうち置換基が
有機基である有機シリレン（：SiR2）を得るに
は各種の方法が知られており、その１つにポリシ
ラン類を光分解する方法がある。この方法は操作
が非常に簡単であることから、応用範囲が広い。 Silylene, a divalent silicon intermediate, is highly reactive and is therefore expected to be particularly useful in new synthetic reactions, and has been widely studied. Among these, various methods are known for obtaining organic silylene (:SiR 2 ) in which the substituent is an organic group, one of which is a method of photolyzing polysilanes. This method has a wide range of applications because it is very easy to operate.
上記の方法の１つに鎖状のフエニルジシラン類
を光分解する方法が知られているが、この方法で
の反応は１，３−ケイ素転位したシラエテン中間
体を経由する反応が主であり、有機シリレンを得
る経路は低収率である。 One of the above methods is known to photodecompose chain phenyldisilanes, but the reaction in this method is mainly via a 1,3-silicon rearranged silaethene intermediate, and the organic The route to silylene is low yield.
本発明の目的は、光分解で有機シリンレンを高
収率で得る新規なフエニルジシラン系化合物およ
びそれを製造する方法を提供するにある。 An object of the present invention is to provide a novel phenyldisilane compound that can obtain organic silylene in high yield by photolysis, and a method for producing the same.
上記目的は、各種のフエニルジシラン系化合物
を合成し、有機シリレンの発生収率を調べた結
果、次式で示される新規なフエニルジシラン系化
合物が有用であることを見い出した
本発明の新規フエニルジシラン系化合物は一般
式、
（式中R1はメチル基を、R2は水素原子を表わ
す）で示される。 For the above purpose, as a result of synthesizing various phenyldisilane compounds and examining the yield of organic silylene, it was found that a new phenyldisilane compound represented by the following formula is useful. The novel phenyldisilane compound of the present invention is general formula, (In the formula, R 1 represents a methyl group and R 2 represents a hydrogen atom.)
本発明の新規フエニルジシラン系化合物として
は、次のものがあげられる。 The novel phenyldisilane compounds of the present invention include the following.
９，９，10，10−テトラメチル−９，10−ジシ
ラ−９，10−ジヒドロフエナントレン。 9,9,10,10-tetramethyl-9,10-disila-9,10-dihydrophenanthrene.
本発明による新規フエニルジシラン系化合物
は、例えば次の方法によつて合成できる。２，
2′−ジブロモビフエニルをアルゴン置換した容器
中でエーテルに溶解し、氷冷した状態で激しく撹
拌しつつ、これにブチルリチウムの２〜2.5モル
をゆつくりと滴下する。滴下終了後温室でさらに
撹拌を続けることによつて、２，2′−ジリチオビ
フエニルが得られる。これをアルゴン置換した容
器中で１，２−ジクロロ−１，１，22−テトラメ
チルジシラン，あるいは１，２−ジブロモ−１，
１，２，２−テトラメチルジシランの１モルをエ
ーテルに溶解したものに撹拌しながら加え、さら
に還流を行う。この操作によつて目的の生成物で
ある９，９，10，10−テトラメチル−９，10−ジ
シラ−９，10−ジヒドロフエナントレンと副生成
物である９，９−ジメチル−９−シラフルオレン
が得られる。これらの分離は蒸留，液体クロマト
グラフイー，ガスクロマトグラフイなどの方法で
行うことがきる。 The novel phenyldisilane compound according to the present invention can be synthesized, for example, by the following method. 2,
2'-dibromobiphenyl is dissolved in ether in a container purged with argon, and 2 to 2.5 moles of butyllithium are slowly added dropwise thereto while stirring vigorously while cooling with ice. After the addition is complete, stirring is continued in the greenhouse to obtain 2,2'-dilithiobiphenyl. 1,2-dichloro-1,1,22-tetramethyldisilane or 1,2-dibromo-1,
1 mole of 1,2,2-tetramethyldisilane dissolved in ether is added with stirring and refluxed. By this operation, the desired product 9,9,10,10-tetramethyl-9,10-disila-9,10-dihydrophenanthrene and the by-product 9,9-dimethyl-9- Silafluorene is obtained. These separations can be performed using methods such as distillation, liquid chromatography, and gas chromatography.
また９，９，10，10−テトラエチル−９，10−
ジシラ−９，10−ジヒドロフエナントレンは上記
の１，２−ジクロロ−１，１，２，２−テトラメ
チルジシランのかわりに１，２−ジクロロテトラ
エチルジシランを用い、その他は上記と同じ方法
で得ることができる。 Also 9,9,10,10-tetraethyl-9,10-
Disila-9,10-dihydrophenanthrene was prepared in the same manner as above except that 1,2-dichlorotetraethyldisilane was used instead of 1,2-dichloro-1,1,2,2-tetramethyldisilane. Obtainable.
次に本発明の実施例を示す。 Next, examples of the present invention will be shown.
実施例 １
100mlの３つ口フラスコをアルゴン置換したの
ち、その中に２，2′−ジブロモビフエニルの4g
（0.0129モル）とエチルエーテルの40mlを加え、
これを氷冷し、スターラーで激しく撹拌しつつ、
これにブチルリチウムの0.925規定ヘキサン溶液
の30.27ml（ブチルリチウムとして0.028モル）を
20分間で滴下し、さらにこれを空冷下、５時間撹
拌した〔反応液Ａ〕。次に別に用意した200mlの３
つ口フラスコをアルゴン置換し、その中に１，２
−ジクロロ−１，１，２，２−テトラメチルジシ
ランの2.4g（0.0129モル）とエチルエーテルの25
mlを加え、これに上記の反応液Ａを撹拌しつつ添
加し、さらに２時間還流させた。これを蒸留した
ところ、無色透明で粘調な液体が分取された。こ
のものの収率は23％であつた。Example 1 After purging a 100 ml three-necked flask with argon, 4 g of 2,2'-dibromobiphenyl was placed in it.
(0.0129 mol) and add 40 ml of ethyl ether;
Cool this on ice and stir vigorously with a stirrer.
Add 30.27ml of a 0.925N hexane solution of butyllithium (0.028 mol as butyllithium) to this.
The mixture was added dropwise over 20 minutes, and the mixture was further stirred for 5 hours under air cooling [Reaction Solution A]. Next, 200ml of 3 prepared separately.
The necked flask was replaced with argon, and 1,2
-2.4 g (0.0129 mol) of dichloro-1,1,2,2-tetramethyldisilane and 25 g of ethyl ether
ml, and the above reaction solution A was added thereto with stirring, and the mixture was further refluxed for 2 hours. When this was distilled, a clear, colorless and viscous liquid was collected. The yield of this product was 23%.
また、この液体が本発明の９，９，10，10−テ
トラメチル−９，10−ジシラ−９，10−ジヒドロ
フエナントレンであることは、核磁気共鳴（′
HNMR），赤外吸収スペクトル（IRスペクト
ル），高分解能マススペクトルにおける次の結果
から確認された。 Furthermore, the fact that this liquid is the 9,9,10,10-tetramethyl-9,10-disila-9,10-dihydrophenanthrene of the present invention indicates that nuclear magnetic resonance ('
This was confirmed from the following results in HNMR), infrared absorption spectrum (IR spectrum), and high-resolution mass spectrum.
(1) ′HNMR（溶媒CCl4）
δ＝0.23ppm（12H，シングレツト）
δ＝7.1〜7.5ppm（8H，マルチプレツト）
(2) IRスペクトルでの特性的吸収波長1415cm-1
（ビフエニルのＣ＝Ｃ伸縮振動）
1250cm-1（Si−CH3変角振動）
1110cm-1（Si−Ｃリングの骨格振動）
(3) 高分解能マススペクトル
C16H20Si2の計算値＝268.1103
実測値＝268.1104(1) 'HNMR (Solvent CCl 4 ) δ=0.23ppm (12H, singlet) δ=7.1~7.5ppm (8H, multiplet) (2) Characteristic absorption wavelength in IR spectrum 1415cm -1
(C=C stretching vibration of biphenyl) 1250cm -1 (Si-CH 3 bending vibration) 1110cm -1 (skeletal vibration of Si-C ring) (3) High-resolution mass spectrum Calculated value of C 16 H 20 Si 2 = 268.1103 Actual value = 268.1104
Claims (1)
す）で示される新規フエニルジシラン系化合物。 ２ 一般式 （式中R2は水素原子を表わす）で示される化
合物と、一般式 （式中Ｘはクロル原子あるいは臭素原子を表わ
す。R1はメチル基を表わす）で示される化合物
を反応させて、一般式 （式中R1はメチル基を、R2は水素原子を表わ
す）で示される新規フエニルジシラン系化合物を
製造する方法。[Claims] 1. General formula A novel phenyldisilane compound represented by the formula (wherein R 1 represents a methyl group and R 2 represents a hydrogen atom). 2 General formula (In the formula, R 2 represents a hydrogen atom) and a compound represented by the general formula (In the formula, X represents a chlorine atom or a bromine atom. R 1 represents a methyl group) is reacted with the general formula A method for producing a novel phenyldisilane compound represented by the formula (wherein R 1 represents a methyl group and R 2 represents a hydrogen atom).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11905381A JPS5821684A (en) | 1981-07-31 | 1981-07-31 | New phenyldisilane compounds and methods for producing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11905381A JPS5821684A (en) | 1981-07-31 | 1981-07-31 | New phenyldisilane compounds and methods for producing them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5821684A JPS5821684A (en) | 1983-02-08 |
| JPH0323557B2 true JPH0323557B2 (en) | 1991-03-29 |
Family
ID=14751733
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11905381A Granted JPS5821684A (en) | 1981-07-31 | 1981-07-31 | New phenyldisilane compounds and methods for producing them |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5821684A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG124249A1 (en) | 2001-12-07 | 2006-08-30 | Sumitomo Chemical Co | New polymer and polymer light-emitting device using the same |
-
1981
- 1981-07-31 JP JP11905381A patent/JPS5821684A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5821684A (en) | 1983-02-08 |
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