JPH01230574A - Production of 1,3-dithiolan-2-one derivative - Google Patents
Production of 1,3-dithiolan-2-one derivativeInfo
- Publication number
- JPH01230574A JPH01230574A JP5719788A JP5719788A JPH01230574A JP H01230574 A JPH01230574 A JP H01230574A JP 5719788 A JP5719788 A JP 5719788A JP 5719788 A JP5719788 A JP 5719788A JP H01230574 A JPH01230574 A JP H01230574A
- Authority
- JP
- Japan
- Prior art keywords
- carbon disulfide
- reaction
- formula
- dithiolan
- reacting
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- ZBEWVJOWXJNDGJ-UHFFFAOYSA-N 1,3-dithiolan-2-one Chemical class O=C1SCCS1 ZBEWVJOWXJNDGJ-UHFFFAOYSA-N 0.000 title claims description 6
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims abstract description 42
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 150000002118 epoxides Chemical class 0.000 claims abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract description 21
- 238000006243 chemical reaction Methods 0.000 abstract description 13
- 150000001875 compounds Chemical class 0.000 abstract description 10
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 239000002994 raw material Substances 0.000 abstract 2
- 239000007810 chemical reaction solvent Substances 0.000 abstract 1
- 230000002498 deadly effect Effects 0.000 abstract 1
- 238000004043 dyeing Methods 0.000 abstract 1
- 231100000614 poison Toxicity 0.000 abstract 1
- 230000007096 poisonous effect Effects 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- NJWSNNWLBMSXQR-UHFFFAOYSA-N 2-hexyloxirane Chemical compound CCCCCCC1CO1 NJWSNNWLBMSXQR-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XCWPBWWTGHQKDR-UHFFFAOYSA-N 1,3-dithiolane-2-thione Chemical compound S=C1SCCS1 XCWPBWWTGHQKDR-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 3
- -1 epoxide compound Chemical class 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- UGBZULJIBDUPFO-UHFFFAOYSA-N 4-phenyl-1,3-dithiolan-2-one Chemical compound S1C(=O)SCC1C1=CC=CC=C1 UGBZULJIBDUPFO-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- HXOYEKUNPUDUPM-UHFFFAOYSA-N 1,3-oxathiolane-2-thione Chemical compound S=C1OCCS1 HXOYEKUNPUDUPM-UHFFFAOYSA-N 0.000 description 1
- LGWWCMYOOVPLER-UHFFFAOYSA-N 4-ethyl-1,3-dithiolan-2-one Chemical compound C(C)C1SC(SC1)=O LGWWCMYOOVPLER-UHFFFAOYSA-N 0.000 description 1
- NFPWEXAVSWIDJE-UHFFFAOYSA-N 4-ethyl-1,3-dithiolane-2-thione Chemical compound CCC1CSC(=S)S1 NFPWEXAVSWIDJE-UHFFFAOYSA-N 0.000 description 1
- YXQDJSKSXLWHFQ-UHFFFAOYSA-N 4-hexyl-1,3-dithiolane-2-thione Chemical compound CCCCCCC1CSC(=S)S1 YXQDJSKSXLWHFQ-UHFFFAOYSA-N 0.000 description 1
- DSLRLRPNJIGHLW-UHFFFAOYSA-N 4-methyl-1,3-dithiolan-2-one Chemical compound CC1CSC(=O)S1 DSLRLRPNJIGHLW-UHFFFAOYSA-N 0.000 description 1
- OVMVMMNHNMZUAS-UHFFFAOYSA-N 4-methyl-1,3-dithiolane-2-thione Chemical compound CC1CSC(=S)S1 OVMVMMNHNMZUAS-UHFFFAOYSA-N 0.000 description 1
- UNAVLWYSWPISLX-UHFFFAOYSA-N 4-phenyl-1,3-dithiolane-2-thione Chemical compound S1C(=S)SCC1C1=CC=CC=C1 UNAVLWYSWPISLX-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 238000000262 chemical ionisation mass spectrometry Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 150000004662 dithiols Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000012970 tertiary amine catalyst Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は、１，３−ジチオラン−２−オン誘導体の製造
法に関するもので、より詳細にはこれらの化合物を、エ
ポキシド化合物と二硫化炭素とを塩基の存在下、高圧で
反応させることにより、簡単にかつ収率よく製是する方
法に関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing 1,3-dithiolan-2-one derivatives, and more specifically, these compounds are prepared by combining an epoxide compound and carbon disulfide in the presence of a base. The present invention relates to a method for easily producing it with high yield by reacting at high pressure.
［産業上の利用分野］
従来、１．３−ジチオラン−２−オンの誘導体数報告さ
れている（Ｊ、Ｈｅｔｅｒｏｃｙｌ Ｃｈｅｍ、ｅ２１
，１８４５（１９８４）、特開昭５５−１２０５０４号
、Ｇｅｒ、０ｆｆａｎ、２，３５７゜９３０）。[Industrial Application Field] A number of derivatives of 1,3-dithiolan-2-one have been reported (J, Heterocyl Chem, e21
, 1845 (1984), JP-A-55-120504, Ger, Offan, 2,357°930).
［発明が解決しようとする問題点コ
このように１，３−ジチオラン−２−オン誘導体は有用
な化合物であるが、現在は１，３−ジチオラン−２−チ
オンと硝酸または酢酸水銀との反応、あるいはジチオー
ル類とホスゲンとの反応などの製造法が知られている。[Problems to be solved by the invention] As described above, 1,3-dithiolan-2-one derivatives are useful compounds, but currently the reaction of 1,3-dithiolan-2-thione with nitric acid or mercuric acetate is Alternatively, production methods such as reaction of dithiols and phosgene are known.
しかし、これらの方法は、１，３−ジチオラン−２−チ
オン類は市販されておらず、−また水への溶解性の悪い
ものが多い、あるいは猛毒のホスゲンを用いなければな
らないなどの問題点があった。However, these methods have problems, such as 1,3-dithiolane-2-thiones are not commercially available, and many have poor solubility in water, or the use of highly toxic phosgene. was there.
したがって、本発明の目的は、１，３−ジチオラン−２
−オン誘導体の効率的な製造方法を開発することである
。Therefore, the object of the present invention is to provide 1,3-dithiolane-2
The object of the present invention is to develop an efficient method for producing -one derivatives.
［問題点を解決するための手段］ ることを見い出し、本発明を完成するの至った。[Means for solving problems] This discovery led to the completion of the present invention.
すなわち１本発明は、
（式中Ｒ１は、アルキル基またはアリール基 ａ２は、
アルキル基または水素原子を示す、）で示されるエポキ
シドと二硫化炭素とを塩基の存在下、高圧をかけて反応
させることを特徴とする（式中Ｒ１およびＲ２１よ、前
記と同じ、）で示される１、３−ジチオラン−２−オン
誘導体の製造方法を提供するものである。That is, 1 of the present invention, (wherein R1 is an alkyl group or an aryl group a2 is
It is characterized by reacting an epoxide represented by (representing an alkyl group or a hydrogen atom) with carbon disulfide in the presence of a base under high pressure (in the formula, R1 and R21 are the same as above). The present invention provides a method for producing a 1,3-dithiolan-2-one derivative.
３−ジチオラン−２−オン誘導体を製造することができ
る。なお、本発明において、 Ｒ’、 Ｒ”は反応に不
活性な置換基で更に置換されている場合も包含する。3-dithiolan-2-one derivatives can be produced. In the present invention, R' and R'' also include cases where they are further substituted with a substituent inert to the reaction.
次に本発明における目的化合物（２）の生成経路を塩基
としてトリエチルアミンを用いた１−オクテンオキシド
と二硫化炭素との反応を例に取れば下記の式（３）のよ
うに表わせる。Next, taking as an example the reaction between 1-octene oxide and carbon disulfide using triethylamine as a base, the production route of the target compound (2) in the present invention can be expressed as shown in the following formula (3).
Ｓ
Ｃｓ Ｈ−３
○ （２）
本発明の反応は通常、第３級アミン触媒の存在下、ヘキ
サンなどの溶媒を用いて高圧条件下で行なわれる。二硫
化炭素を大過剰に用いたり、反応を初期でとめたりした
場合には生成物は１，３−ジチオラン−２−チオンおよ
び１，３−オキサチオラン−２−チオンのみが得られ（
特願昭６２−５２７４８号）、目的の化合物（２）は生
成しない。S Cs H-3 ○ (2) The reaction of the present invention is usually carried out under high pressure conditions using a solvent such as hexane in the presence of a tertiary amine catalyst. If carbon disulfide is used in large excess or the reaction is stopped early, only 1,3-dithiolane-2-thione and 1,3-oxathiolane-2-thione are obtained as products (
(Japanese Patent Application No. 62-52748), the target compound (2) is not produced.
しかし、エポキシＪ−’ （１）と二硫化炭素とをほぼ
等モル用い、ヘキサンなどの溶媒で稀釈して反応させる
と反応後期に化合物（２）が急激に生成する。However, when epoxy J-' (1) and carbon disulfide are used in approximately equal moles and reacted by diluting with a solvent such as hexane, compound (2) is rapidly generated in the latter stage of the reaction.
範囲で選択される０反応温度は特に制約されないが副反
応の進行を抑制する意味では室温〜１２０℃の温度の採
用が好ましい０反応時間は圧力、温度などに左右される
が１通常５〜５０時間で十分である０反応混合物から溶
媒を留去した後、減圧蒸留することにより本発明の目的
化合物が収率よく得られる。かくして得られた目的化合
物は、必要に応じぞカラムクロマトグラフィーにより分
離し、ＩＲ，ＮＭＲ，ＭＳを分析することによりその構
造を確認できる。0 Reaction temperature selected within the range is not particularly restricted, but in the sense of suppressing the progress of side reactions, it is preferable to adopt a temperature of room temperature to 120 ° C. 0 Reaction time depends on pressure, temperature, etc. 1 Usually 5 to 50 °C The target compound of the present invention can be obtained in good yield by distilling off the solvent from the reaction mixture for a sufficient time and then distilling it under reduced pressure. The target compound thus obtained can be separated by column chromatography if necessary, and its structure can be confirmed by analyzing IR, NMR, and MS.
［発明の効果コ
本発明によれば、あまり市販されていない１゜３−ジチ
オラン−２−チオンの誘導体や猛毒なホスゲンを用いる
ことなく、種々の置換体が寝息に入手できるエポキシド
と二硫化炭素を用いて、１゜３−ジチオラン−２−オン
の誘導体を一段階で高が可能である。[Effects of the Invention] According to the present invention, epoxides and carbon disulfide can be easily obtained with various substituents without using derivatives of 1゜3-dithiolane-2-thione, which are not commercially available, or extremely toxic phosgene. Using this method, it is possible to prepare a derivative of 1°3-dithiolan-2-one in one step.
［実施例コ 本発明を実施例に基づき、更に詳細に説明する。[Example code] The present invention will be explained in more detail based on examples.
実施例１
テフロンチューブに１−オクテンオキシド０゜６４ｇ、
トリエチルアミン０．０５ｇ、二硫化炭素０．３８
ｇ、ヘキサン３１１１を封入し、高圧反応装置ニ入れて
、８０００ ｋ ｇ／ｃｘｌＬ：、加圧し１００℃で２
００時間反応た。圧を常圧に戻した後、反応物を取り出
し、溶媒を留去した。残留物を減圧蒸留することにより
、４−へキシル−１，３−ジチオラン−２−オン３６２
．７％、４−へキシル−１，３−ジチオラン−２−チオ
ンを１５．５％の収率で得た。これらの化合物はシリカ
ゲルを用いたカラムクロマトグラフィー（ヘキサン：ク
ロＣＩ−ＭＳによるＱＭ” ； ２０５ＮＭＲ：
０．８９（ｔ、３Ｈ，ＣＨ，）、 １．３１（ｓ、８
１１．＋ＣＨａ＋＊ｔ１．６５〜２．１０（ｌｌ、２Ｈ
，ＣＨ２）、３−２４〜３．８６（ｍ、２Ｈ９ＣＨ１＞
９３．９１〜４．３７（ｍ、１８．ＣＨ）実施例２
前記と同様にして、１−オクテンオキシド０゜６４ｇ、
Ｎ−メチルモルホリン０．０５ｇ、二硫化炭素０．３８
ｇ、ヘキサン３ｍｌを、８０００ｋｇ／ａ＃、１００℃
で７時間反応させた。前記と同様の処理により、４−へ
キシル−１，３−ジチオラン−２−オンを５９．８％、
４−ヘキシル−１゜３−ジチオラン−２−チオンを１５
．５％の収率で得た。Example 1 0°64g of 1-octene oxide in a Teflon tube,
Triethylamine 0.05g, carbon disulfide 0.38
g, Hexane 3111 was sealed, put into a high pressure reactor, 8000 kg/cxlL:, pressurized and heated at 100℃.
It reacted for 00 hours. After returning the pressure to normal pressure, the reaction product was taken out and the solvent was distilled off. By distilling the residue under reduced pressure, 4-hexyl-1,3-dithiolan-2-one 362
．． 7%, 4-hexyl-1,3-dithiolane-2-thione was obtained in a yield of 15.5%. These compounds were analyzed by column chromatography using silica gel (hexane: QM by chromatography CI-MS; 205NMR:
0.89 (t, 3H, CH,), 1.31 (s, 8
11. +CHa+*t1.65~2.10(ll, 2H
, CH2), 3-24 to 3.86 (m, 2H9CH1>
93.91-4.37 (m, 18.CH) Example 2 In the same manner as above, 0°64 g of 1-octene oxide,
N-methylmorpholine 0.05g, carbon disulfide 0.38
g, 3ml of hexane, 8000kg/a#, 100℃
The mixture was allowed to react for 7 hours. By the same treatment as above, 59.8% of 4-hexyl-1,3-dithiolan-2-one,
15 4-hexyl-1゜3-dithiolane-2-thione
．． Obtained with a yield of 5%.
実施例３
前記と同様にして、１−オクテンオキシド０゜６４ｇ、
トリエチルアミン０．０５ｇ、二硫化炭３−ジチオラン
ー２−チオンを１７．３％の収率で得た。Example 3 In the same manner as above, 0.64 g of 1-octene oxide,
0.05 g of triethylamine and carbon disulfide 3-dithiolane-2-thione were obtained in a yield of 17.3%.
実施例４
前記と同様にして、プロピレンオキシド０．２９ｇ、ト
リエチルアミン０．０５ｇ、二硫化炭素０．３８ｇ、ヘ
キサン３ｍｌを、５０００ ｋ ｇ／ｃｉ。Example 4 In the same manner as above, 0.29 g of propylene oxide, 0.05 g of triethylamine, 0.38 g of carbon disulfide, and 3 ml of hexane were mixed at 5000 kg/ci.
１００℃で２００時間反応せた。前記と同様の処理によ
り、４−メチル−１，３−ジチオラン−２−オンを２２
．４％、４−メチル−１，３−ジチオラン−２−チオン
を４４．０％の収率で得た。The reaction was carried out at 100°C for 200 hours. By the same treatment as above, 4-methyl-1,3-dithiolan-2-one was converted to 22
．． 4%, 4-methyl-1,3-dithiolane-2-thione was obtained in a yield of 44.0%.
−先二％ｆソ乞二よ、」二づとＬオン）宜二【ニオツー
Ｉ Ｒ； １７１３ａｍ−１，１６４２ａｌ−’ＮＭ
Ｒ； １．６０（ｄ、３Ｈ，ＣＨ，）。- 2% f so beg for you, ``2nd L on) Giji [Nio2 I R; 1713am-1, 1642al-'NM
R; 1.60 (d, 3H, CH,).
３．２２〜３．５３（ｄｄ、ＩＨ，ＣＨ，のｌプロトン
）。3.22-3.53 (1 proton of dd, IH, CH,).
３．５８〜３．８５（ｄｄ、ＬＨ，Ｃ）１．の１プロト
ン）。3.58-3.85 (dd, LH, C)1. 1 proton).
４．００〜４．４２（ｍ、ＩＨ，ＣＨ）１００℃で２０
０時間反応せた。前記と同様の処理により、４−エチル
−１，３−ジチオラン−２−オンを４７．３％、４−エ
チル−１，３−ジチオラン−２−チオンを２４．４％の
収率で得た。4.00-4.42 (m, IH, CH) 20 at 100℃
The reaction was allowed to proceed for 0 hours. By the same treatment as above, 4-ethyl-1,3-dithiolane-2-one was obtained in a yield of 47.3% and 4-ethyl-1,3-dithiolane-2-thione was obtained in a yield of 24.4%. .
土二Ｚ ｆ ／ｌ仁二辷工且二乏ｌ」ゴじ仁二互ニオツ
ーＩ Ｒ； １７２５ａｍ−Ｌ、１６４２ａｉ−’Ｎ
ＭＲ； １．０６（ｔ、３Ｈ，ＣＨ，）、 １．９３
（ｇｕｉｎ、２Ｈ，Ｃｌ２）３．３０〜３．５６（ｄｄ
、ＣＨｚの１プロトン）。1725am-L, 1642ai-'N
MR; 1.06 (t, 3H, CH,), 1.93
(guin, 2H, Cl2) 3.30-3.56 (dd
, 1 proton in CHz).
３．６０〜３．８７（ｄｄ、 ＩＨ，ＣＨ，の１プロト
ン）。3.60-3.87 (dd, 1 proton of IH, CH,).
３．８９−４．２２（ｍ、ＩＨ，ＣＩ）実施例６
前記と同様にして、イソブチンオキシド０．３６ｇ、ト
リエチルアミン０．０５ｇ、二硫化炭素０．３８ｇ、ヘ
キサン３１１１を、５０００ｋｇ／ａＪ、１００℃で２
０時間反応させた。前記と同様の処理により、４，４−
ジメチル−１，３−ジチオラＩＲ： １７２５ａａ−
’、１６４３ｍ−”ＮＭＲ； １．７０（ｓ、６８，
２ＣＨ３）、 ３．４７（ｓ、２Ｈ２Ｃ１ｌａ）実施例
７
前記と同様にして、スチレンオキシド０．６０ｇ、トリ
エチルアミン０．０５ｇ、二硫化炭素０゜３８ｇ、ヘキ
サン３１を、５０００ｋｇ／ａｊ、１００℃で２０時間
反応させた。前記と同様の処理により、４−フェニル−
１，３−ジチオラン−２−オンを９．２％、４−フェニ
ル−１，３−ジチオラン−２−チオンを４８．１％の収
率で得た。3.89-4.22 (m, IH, CI) Example 6 In the same manner as above, 0.36 g of isobutyne oxide, 0.05 g of triethylamine, 0.38 g of carbon disulfide, and 3111 hexane were added at 5000 kg/aJ, 2 at 100℃
The reaction was allowed to proceed for 0 hours. By the same treatment as above, 4,4-
Dimethyl-1,3-dithiola IR: 1725aa-
', 1643m-'NMR; 1.70 (s, 68,
2CH3), 3.47(s, 2H2C1la) Example 7 In the same manner as above, 0.60 g of styrene oxide, 0.05 g of triethylamine, 0.38 g of carbon disulfide, and 31 hexane were mixed at 5000 kg/aj at 100°C for 20 Allowed time to react. By the same treatment as above, 4-phenyl-
1,3-dithiolane-2-one was obtained in a yield of 9.2%, and 4-phenyl-1,3-dithiolane-2-thione was obtained in a yield of 48.1%.
４−フェニル−１，３−ジチオラン−２−オンＩ Ｒ；
１７３３ａｍ−”、１６５１ａｓ−”ＮＭＲ；
３．８４（ｄ、２１１．ＣＨ，）、 ５．２４（ｔ、Ｉ
ＩＩ、Ｃ１（）。4-phenyl-1,3-dithiolan-2-one I R;
1733am-", 1651as-"NMR;
3.84 (d, 211.CH,), 5.24 (t, I
II, C1 ().
Claims (1)
・・（１） （式中Ｒ＾１は、アルキル基またはアリール基、Ｒ＾２
は、アルキル基または水素原子を示す。）で示されるエ
ポキシドと二硫化炭素とを塩基の存在下、高圧をかけて
反応させることを特徴とする 一般式 ▲数式、化学式、表等があります▼・・・・・・・・・
・・（２） （式中Ｒ＾１およびＲ＾２は、前記と同じ。）で示され
る１，３−ジチオラン−２−オン誘導体の製造方法。(1) General formula▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・・・・
...(1) (In the formula, R^1 is an alkyl group or an aryl group, R^2
represents an alkyl group or a hydrogen atom. ) is a general formula characterized by reacting the epoxide shown by carbon disulfide with carbon disulfide in the presence of a base under high pressure▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・・・・
...(2) A method for producing a 1,3-dithiolan-2-one derivative represented by the formula (wherein R^1 and R^2 are the same as above).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5719788A JPH01230574A (en) | 1988-03-10 | 1988-03-10 | Production of 1,3-dithiolan-2-one derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5719788A JPH01230574A (en) | 1988-03-10 | 1988-03-10 | Production of 1,3-dithiolan-2-one derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01230574A true JPH01230574A (en) | 1989-09-14 |
| JPH0415233B2 JPH0415233B2 (en) | 1992-03-17 |
Family
ID=13048765
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5719788A Granted JPH01230574A (en) | 1988-03-10 | 1988-03-10 | Production of 1,3-dithiolan-2-one derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01230574A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012214386A (en) * | 2011-03-31 | 2012-11-08 | Wako Pure Chem Ind Ltd | Method for producing cyclic trithiocarbonate |
-
1988
- 1988-03-10 JP JP5719788A patent/JPH01230574A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012214386A (en) * | 2011-03-31 | 2012-11-08 | Wako Pure Chem Ind Ltd | Method for producing cyclic trithiocarbonate |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0415233B2 (en) | 1992-03-17 |
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