JPH02250836A - Benzylating agent and benzylation of thiol - Google Patents
Benzylating agent and benzylation of thiolInfo
- Publication number
- JPH02250836A JPH02250836A JP7125489A JP7125489A JPH02250836A JP H02250836 A JPH02250836 A JP H02250836A JP 7125489 A JP7125489 A JP 7125489A JP 7125489 A JP7125489 A JP 7125489A JP H02250836 A JPH02250836 A JP H02250836A
- Authority
- JP
- Japan
- Prior art keywords
- benzylation
- group
- thiol
- compound
- halogen
- 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.)
- Granted
Links
- 238000005574 benzylation reaction Methods 0.000 title claims abstract description 16
- 125000003396 thiol group Chemical class [H]S* 0.000 title claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 14
- -1 benzyl-4-hydroxyphenylmethylsulfonium compound Chemical class 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 7
- 235000018417 cysteine Nutrition 0.000 claims abstract description 5
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims abstract description 5
- 108090000765 processed proteins & peptides Proteins 0.000 claims abstract description 5
- 235000018102 proteins Nutrition 0.000 claims abstract description 5
- 102000004169 proteins and genes Human genes 0.000 claims abstract description 5
- 108090000623 proteins and genes Proteins 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 125000005489 p-toluenesulfonic acid group Chemical group 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 15
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract description 6
- 239000002585 base Substances 0.000 abstract description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 4
- 229910001854 alkali hydroxide Inorganic materials 0.000 abstract description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract description 2
- 239000007853 buffer solution Substances 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- 150000002367 halogens Chemical class 0.000 abstract description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical group OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 abstract description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 2
- 150000003573 thiols Chemical class 0.000 abstract 2
- 229910017048 AsF6 Inorganic materials 0.000 abstract 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical compound COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- GHBAYRBVXCRIHT-VIFPVBQESA-N S-benzyl-L-cysteine zwitterion Chemical compound OC(=O)[C@@H](N)CSCC1=CC=CC=C1 GHBAYRBVXCRIHT-VIFPVBQESA-N 0.000 description 5
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229960002433 cysteine Drugs 0.000 description 3
- LEVWYRKDKASIDU-IMJSIDKUSA-N L-cystine Chemical compound [O-]C(=O)[C@@H]([NH3+])CSSC[C@H]([NH3+])C([O-])=O LEVWYRKDKASIDU-IMJSIDKUSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229960003067 cystine Drugs 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 102000004196 processed proteins & peptides Human genes 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- QIJRTFXNRTXDIP-UHFFFAOYSA-N (1-carboxy-2-sulfanylethyl)azanium;chloride;hydrate Chemical compound O.Cl.SCC(N)C(O)=O QIJRTFXNRTXDIP-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 1
- 125000006307 alkoxy benzyl group Chemical group 0.000 description 1
- 125000006177 alkyl benzyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 150000001450 anions Chemical group 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229960001305 cysteine hydrochloride Drugs 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
Abstract
Description
【発明の詳細な説明】
〈産業上の利用分野〉
本発明は新規なベンジル化剤、及び当該ベンジル化剤に
よるチオール基を有する化合物のベンジル化方法に関す
る。更に詳しくは、特定のスルホニウム塩によるベンジ
ル化剤、及び当該ベンジル化剤によるチオール基を有す
る化合物のベンジル化方法に関する。DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to a novel benzylating agent and a method for benzylating a compound having a thiol group using the benzylating agent. More specifically, the present invention relates to a benzylating agent using a specific sulfonium salt and a method for benzylating a compound having a thiol group using the benzylating agent.
〈従来技術〉
従来、チオール基のベンジル化方法としては、たとえば
ペプチド性医薬品原料として有用であるＳ−ベンジルシ
スティンの製造方法に代表されるように、ベンジル化剤
として塩化もしくは臭化ベンジルを塩基存在下、反応さ
せていた。しかしながらこれらの試薬は非常に刺激性で
あり、極めて取扱い難く、しかもその反応は激しいため
にジスルフィド等の生成といっな副反応が進行するなど
、目的物の収率も満足いくものではない。<Prior art> Conventionally, as a method for benzylating a thiol group, as typified by the method for producing S-benzylcysteine, which is useful as a raw material for peptide pharmaceuticals, benzyl chloride or bromide is used as a benzylating agent in the presence of a base. Below, I was reacting. However, these reagents are extremely irritating and extremely difficult to handle, and their reactions are so violent that side reactions such as the formation of disulfides proceed, resulting in unsatisfactory yields of the desired product.
特に生化学分野においてペプチド、タンパク質中のチオ
ール基を、副反応を避けつつベンジル化することは、タ
ンパク質の構造上、あるいはその性質上、従来の試薬で
は不可能と言える。Particularly in the field of biochemistry, it is impossible to benzylate thiol groups in peptides and proteins while avoiding side reactions using conventional reagents due to the structure or properties of proteins.
く本発明が解決しようとする問題点〉
従来知られているベンジル化方法には、前述のような欠
点が存在する。本発明は、穏和な条件下、刺激臭もなく
、簡便かつ高収率でチオール基をベンジル化させるベン
ジル化剤、ならびにベンジル化方法を提供することを目
的とする。なお、ここで言うベンジル基には各種の置換
ベンジル基が含まれることは言うまでもない。例えば、
ハロゲン化ベンジル基、ニトロ化ベンジル基、アルキル
ベンジル基、アルコキシベンジル基等が当然含まれる。Problems to be Solved by the Present Invention> Conventionally known benzylation methods have the above-mentioned drawbacks. An object of the present invention is to provide a benzylating agent and a benzylation method that can benzylate a thiol group simply and in high yield under mild conditions without any irritating odor. It goes without saying that the benzyl group referred to herein includes various substituted benzyl groups. for example,
Naturally, halogenated benzyl groups, nitrated benzyl groups, alkylbenzyl groups, alkoxybenzyl groups, and the like are included.
（以下成葉）
〈問題点を解決するための手段〉
本発明は一般式
（式中Ｒ１，Ｒ２はそれぞれ独立して、水素、アルキル
基、アルコキシ基、ハロゲン基、ニトロ基を示す。Ｘは
、ハロゲン、過塩素酸基、ＳｂＦ６゜ＡｓＦｇ、ＰＦ６
．ＢＦ４．メチル硫酸、ｐ−トルエンスルホン酸基を示
す）
で表わされるベンジル化剤、ならびにチオール化合物の
ベンジル化方法である。さらに述べれば、上記スルホニ
ウム化合物によるベンジル化剤、及び上記スルホニウム
化合物とチオール基を有する化合物とを塩基存在下反応
させることによる、簡１更かつ高収率でチオール基をベ
ンジル化する方法に関するものである。(hereinafter referred to as adult leaves) <Means for solving the problems> The present invention is based on the general formula (wherein R1 and R2 each independently represent hydrogen, an alkyl group, an alkoxy group, a halogen group, or a nitro group. , halogen, perchlorate group, SbF6゜AsFg, PF6
．． BF4. methyl sulfate, p-toluenesulfonic acid group); and a method for benzylating a thiol compound. More specifically, the present invention relates to a method for benzylating a thiol group simply and in high yield by reacting the above-mentioned benzylating agent with a sulfonium compound and the above-mentioned sulfonium compound and a compound having a thiol group in the presence of a base. be.
本発明の方法に従えば、穏和条件下でベンジル化反応が
進行するために、生体成分の化学修飾への適用も期待で
きる。また、本発明の試薬は無臭の安定な白色結晶であ
り、その使用方法は極めて簡便である。ここで反応基質
として使用されるチオール化合物としてはシスティンに
代表されるアミノ酸、アルキルメルカプタン、芳香族メ
ルカプタン等のメルカプタン類、ペプチド類、タンパク
質が例示される。また本発明に用いられる塩基としては
、ピリジン、トリエチルアミン。According to the method of the present invention, since the benzylation reaction proceeds under mild conditions, it can be expected to be applied to the chemical modification of biological components. Furthermore, the reagent of the present invention is an odorless and stable white crystal, and its method of use is extremely simple. Examples of the thiol compound used as a reaction substrate include amino acids represented by cysteine, mercaptans such as alkyl mercaptans and aromatic mercaptans, peptides, and proteins. Further, examples of the base used in the present invention include pyridine and triethylamine.
Ｎ−メチルモルホリンなどの有機アミン類、および水酸
化アルカ１九炭酸アルカリ、重炭酸アルカリなどの無機
塩基があげられる。また、上記−最式で示されるベンジ
ル化剤の使用されるｐＨは、６．０〜１２．０が好まし
い。従ってこのｐＨを維持するために、いわゆる緩衝液
中で反応させるのが好ましい。反応温度は４０℃以下が
好ましい。Examples include organic amines such as N-methylmorpholine, and inorganic bases such as alkali hydroxides, alkali carbonates, and alkali bicarbonates. Moreover, the pH at which the benzylating agent shown by the above formula is used is preferably 6.0 to 12.0. Therefore, in order to maintain this pH, it is preferable to carry out the reaction in a so-called buffer solution. The reaction temperature is preferably 40°C or lower.
４０℃を越えると、上記一般式で示されるベンジル化剤
がしだいに熱分解を起こすが、反応そのものは進行する
。反応溶媒としては、基質であるチオール化合物を溶解
させる溶媒であれば、本発明の試薬は必ずしも溶解する
必要はなく、懸濁状態であったとしても充分反応は進行
する。反応時間は１〜数時間程度であり、均一あるいは
不均一反応後、反応残渣を水洗し、次いでアルコール洗
浄等により、未反応のベンジル化剤が分離され、ベンジ
ル化された化合物が容易に得られる。When the temperature exceeds 40°C, the benzylating agent represented by the above general formula gradually undergoes thermal decomposition, but the reaction itself proceeds. The reaction solvent does not necessarily need to dissolve the reagent of the present invention, as long as it can dissolve the thiol compound that is the substrate, and the reaction will proceed satisfactorily even if it is in a suspended state. The reaction time is about 1 to several hours, and after the homogeneous or heterogeneous reaction, the reaction residue is washed with water and then washed with alcohol, etc. to separate the unreacted benzylated agent and easily obtain the benzylated compound. .
〈実施例〉
次に本発明を実施例に基き詳細に説明するが、本発明は
実施例により限定されるものではない。<Examples> Next, the present invention will be explained in detail based on Examples, but the present invention is not limited by the Examples.
実施例
Ｓ−ベンジルシスティンの合成
システィン１．２１ ｇに各種塩基をシスティンに対し
て１等量分を加え、水５ｍｌおよびメタノール１０ｍ１
からなる溶液中、室温で１０分撹拌する。Example S - Synthesis of benzylcysteine To 1.21 g of cysteine, add 1 equivalent amount of various bases to cysteine, add 5 ml of water and 10 ml of methanol.
Stir in a solution consisting of for 10 minutes at room temperature.
次いでベンジル−４−ヒドロキシフェニルメチルスルホ
ニウム化合物（アニオン部は別記）１当量分を徐々に加
え、３時間室温で撹拌した。水洗、メタノール洗浄後、
ろ取、乾燥してＳ−ベンジルシスティンを得た。その結
果を表１に示す。Next, 1 equivalent of benzyl-4-hydroxyphenylmethylsulfonium compound (anion part is described separately) was gradually added, and the mixture was stirred at room temperature for 3 hours. After washing with water and methanol,
It was filtered and dried to obtain S-benzylcysteine. The results are shown in Table 1.
なお、いずれの場合でもシスチンの存在は、ＨＰＬＣで
は認められなかった。また、工程中、臭気の発生はなか
った。In any case, the presence of cystine was not observed by HPLC. Furthermore, no odor was generated during the process.
比較例
臭化ベンジルを用いるＳ−ベンジルシスティンの合成
システィン塩酸塩１．５７ ｇを２Ｎ−ＮａＯＨ１２０
ｍｌに溶解し、水冷下に激しくかきまぜながら臭化ベン
ジル２．５６ｇ（１，５当量）を加え、水冷下、数時間
かきまぜて均一な溶液となした。酢酸でｐＨを５．０に
規正し、生成した沈殿をろ取して水洗した。収量１．３
７ｇ（６５％）で、Ｓ−ベンジルシスティンを得た。反
応工程中、継続して臭化ベンジルの刺激臭が認められた
。得られた結晶は刺激性が認められ、臭化ベンジルが若
干混入している。また、ＨＰＬＣによりシスチンの含有
量は２．１％であった。Comparative Example Synthesis of S-benzylcysteine using benzyl bromide 1.57 g of cysteine hydrochloride was dissolved in 2N-NaOH120
ml, and while stirring vigorously under water cooling, 2.56 g (1.5 equivalents) of benzyl bromide was added, and the mixture was stirred for several hours under water cooling to form a homogeneous solution. The pH was adjusted to 5.0 with acetic acid, and the resulting precipitate was collected by filtration and washed with water. Yield 1.3
7g (65%) of S-benzylcysteine was obtained. During the reaction process, a pungent odor of benzyl bromide was continuously observed. The obtained crystals were found to be irritating and contained some benzyl bromide. Further, the cystine content was found to be 2.1% by HPLC.
〈発明の効果〉
本発明のベンジル化剤ならびにベンジル化方法によれば
、チオール基のベンジル化反応が穏和な条件下、簡便か
つ高収率で実施できる。<Effects of the Invention> According to the benzylation agent and benzylation method of the present invention, the benzylation reaction of a thiol group can be carried out easily and in high yield under mild conditions.
Claims (4)
キル基、アルコキシ基、ハロゲン基、ニトロ基を示す。 Ｘは、ハロゲン、過塩素酸基、ＳｂＦ＿６、ＡｓＦ＿６
、ＰＦ＿６、ＢＦ＿４、メチル硫酸、ｐ−トルエンスル
ホン酸基を示す）で表わされるスルホニウム塩によるベ
ンジル化剤(1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, R_1 and R_2 each independently represent hydrogen, an alkyl group, an alkoxy group, a halogen group, or a nitro group. X is a halogen or perchlorine group. Acid group, SbF_6, AsF_6
, PF_6, BF_4, methyl sulfate, p-toluenesulfonic acid group) benzylation agent using a sulfonium salt
スルホニウム塩を塩基存在下チオール基を有する化合物
と反応させることを特徴とするチオール化合物のベンジ
ル化方法(2) A method for benzylating a thiol compound, which comprises reacting a sulfonium salt represented by the general formula described in claim 1 with a compound having a thiol group in the presence of a base.
むペプチド、タンパク質であることを特徴とする特許請
求の範囲第２項記載のベンジル化方法(3) The benzylation method according to claim 2, wherein the thiol compound is a peptide or protein containing cysteine and its residue.
〜１２であることを特徴とする特許請求の範囲第２項記
載のベンジル化方法(4) The pH of the reaction solution described in claim 2 is 6.
The benzylation method according to claim 2, characterized in that the benzylation method is
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7125489A JP2640532B2 (en) | 1989-03-22 | 1989-03-22 | Benzylating agent and method for benzylating thiol compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7125489A JP2640532B2 (en) | 1989-03-22 | 1989-03-22 | Benzylating agent and method for benzylating thiol compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02250836A true JPH02250836A (en) | 1990-10-08 |
| JP2640532B2 JP2640532B2 (en) | 1997-08-13 |
Family
ID=13455390
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7125489A Expired - Lifetime JP2640532B2 (en) | 1989-03-22 | 1989-03-22 | Benzylating agent and method for benzylating thiol compounds |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2640532B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995024387A1 (en) * | 1994-03-09 | 1995-09-14 | Nippon Soda Co., Ltd. | Sulfonium salt compound and polymerization initiator |
| WO2000014059A1 (en) * | 1998-09-08 | 2000-03-16 | Celanese Ventures Gmbh | Method for producing derivatives of 4-alkylsulfinyl methylarylene methanols |
-
1989
- 1989-03-22 JP JP7125489A patent/JP2640532B2/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995024387A1 (en) * | 1994-03-09 | 1995-09-14 | Nippon Soda Co., Ltd. | Sulfonium salt compound and polymerization initiator |
| US5798396A (en) * | 1994-03-09 | 1998-08-25 | Nippon Soda Co., Ltd. | Sulfonium salt-containing compounds and initiators of polymerization |
| WO2000014059A1 (en) * | 1998-09-08 | 2000-03-16 | Celanese Ventures Gmbh | Method for producing derivatives of 4-alkylsulfinyl methylarylene methanols |
| US7087787B1 (en) | 1998-09-08 | 2006-08-08 | Covion Organic Semiconductors Gmbh | Method for producing derivatives of 4-alkylsulfinyl methylarylene methanols |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2640532B2 (en) | 1997-08-13 |
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