JPH0355451B2 - - Google Patents
Info
- Publication number
- JPH0355451B2 JPH0355451B2 JP59110231A JP11023184A JPH0355451B2 JP H0355451 B2 JPH0355451 B2 JP H0355451B2 JP 59110231 A JP59110231 A JP 59110231A JP 11023184 A JP11023184 A JP 11023184A JP H0355451 B2 JPH0355451 B2 JP H0355451B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- hydrogen
- nmr
- tert
- 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 - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 13
- 150000003457 sulfones Chemical class 0.000 claims description 8
- -1 tetrahydropyranyloxy group Chemical group 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 229910052700 potassium Inorganic materials 0.000 claims description 5
- 239000011591 potassium Substances 0.000 claims description 5
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 1
- FVJPIFWJQUIPNO-UHFFFAOYSA-N 2-methylpropan-2-ol;oxolane Chemical compound CC(C)(C)O.C1CCOC1 FVJPIFWJQUIPNO-UHFFFAOYSA-N 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000006326 desulfonation Effects 0.000 description 1
- 238000005869 desulfonation reaction Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000005906 dihydroxylation reaction Methods 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 150000002641 lithium Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
(発明の技術分野)
本発明は共役した炭素、炭素不飽和結合を有す
る化合物の新規製法に関する。
(従来の技術)
共役した炭素、炭素不飽和結合を有する化合物
は有機半導体への特性から興味ある物質であり、
またイソプレノイド系の共役ポリエン化合物はビ
タミンAの前駆物質或いはその他の生理活性物質
もしくはそれらの前駆体として重要である。
従来このような共役不飽和化合物の製法として
は、段階的な二重結合もしくは三重結合の生成或
いは炭素−炭素結合の形成による共役鎖の延長等
合成的に不便な方法しか知られていない。
(発明の目的)
本発明は、スルホニル基に対してβ−位置に、
保護されたヒドロキシ基を有する化合物を用い
て、脱スルホン化と脱ヒドロキシ化を簡便で且つ
穏和な条件下で一挙に行い、有用な共役不飽和化
合物を容易に合成する方法を提供するものであ
る。
(発明の構成)
本発明は、スルホニル基に対してβ位置に、保
護されたヒドロキシ基を有する下記一般式()
で表わされるスルホン類を第三ブトキシカリウム
で処理することを特徴とする共役不飽和化合物の
製法である。
但し、()式において、Yは−CH=CH−又
は−C≡C−、Rはフエニル基、R1は第三ブト
キシカリウムに対して不活性な置換基を有してい
てもよい脂肪族炭化水素基、R2は水素又はR1と
同様に定義される基、R3は水素又はテトラヒド
ロピラニルオキシ基、R4はアセチル基又はテト
ラヒドロピラニル基、nは0又は正整数である。
本発明を反応式で示すと下記()式のように
表わされる。
上記()式のように、本発明は出発物質であ
るスルホン類の炭素骨格中の不飽和結合の共役鎖
を2ケ延長する合成法といえる。例えば、n=0
の場合はジエン化合物が生成し、n=1の場合
は、Yが二重結合のときは生成物はトリエン化合
物となり、Yは三重結合のときはエン−イン−エ
ン化合物が生成する。また本発明の大きな特徴と
して、生成する二重結合はトランス型異性体の生
成率が極めて高いことであり、化合物によつては
実質的に100%のトランス型生成率を示すものが
ある。
本発明において、出発物質として用いられるβ
−位置に、保護されたヒドロキシ基を有するスル
ホン類は、例えば下記()式に示されるように
適当のスルホニル基を有する化合物とアルデヒド
との付加によつて容易に合成することができる。
()式に従つて説明すると、適当なスルホン
を例えばn−ブチル化リチウム(n−BuLi)に
よつてアニオン化してアルデヒドと反応させ、得
られたヒドロキシ化合物を、例えば無水酢酸
(Ac2O)+ピリジン(Py)を作用させる常法によ
つてヒドロキシ基に保護基(アセチル基)を導入
することができる。保護基としては、有機合成反
応で常用されるアセチル基、テトラヒドロピラニ
ル基が用いられる。
本発明のポリエン形成反応は、前記()式に
示したように、スルホニル基とβ−ヒドロキシ基
の脱離反応によるものであり反応は極めて容易で
ある。即ち、出発物質であるスルホン類をテトラ
ヒドロフランもしくはテトラヒドロフラン−第三
ブタノール混合物等を溶媒として第三ブトキシカ
リウムを作用させることによつて目的が達成され
る。
この際、出発物質()式化合物は、R1が強
アルカリである第三ブトキシカリウムと作用しな
い置換基、例えばエチレンジオキシ基、テトラヒ
ドロピラニルオキシ基等の置換を有していてもよ
い脂肪族炭化水素基であり、R2が水素か、又は
上記R1と同様な脂肪族炭化水素基である化合物
であらねばならない。
第三ブトキシカリウムは、スルホン1モルに対
して当量以上、通常2.5〜15モル程度使用される。
反応温度は室温乃至還流温度で十分であり、反応
時間は使用するスルホン類によつて異なり得に制
限されない。
(実施例)
実施例 1〜7
表1に示す出発物質を用いて対応する共役不飽
和化合物を製造した。
表中、t−BuOK(第三ブトキシカリウム)モ
ル比はt−BuOK/出発物質で表をした。生成物
の収率はカラムクロマトグラフイ精製による値で
ある。また、THFはテトラヒドロフラン、t−
BuOHは第三ブタノール、THPはテトラヒドロ
ピラニル基、Phはフエニル基、Acはアセチル
基、Meはメチル基をそれぞれ表わす。
(Technical Field of the Invention) The present invention relates to a novel method for producing compounds having conjugated carbon and carbon unsaturated bonds. (Prior art) Compounds having conjugated carbon and carbon unsaturated bonds are interesting substances due to their properties as organic semiconductors.
Further, isoprenoid-based conjugated polyene compounds are important as precursors of vitamin A or other physiologically active substances or their precursors. Conventionally, only synthetically inconvenient methods have been known for producing such conjugated unsaturated compounds, such as stepwise formation of double or triple bonds or elongation of conjugated chains by formation of carbon-carbon bonds. (Object of the invention) The present invention provides that, in the β-position relative to the sulfonyl group,
The present invention provides a method for easily synthesizing useful conjugated unsaturated compounds by carrying out desulfonation and dehydroxylation at once under simple and mild conditions using a compound having a protected hydroxy group. . (Structure of the Invention) The present invention relates to the following general formula () having a protected hydroxy group at the β position relative to the sulfonyl group.
This is a method for producing a conjugated unsaturated compound, which is characterized by treating a sulfone represented by the formula with potassium tert-butoxy. However, in formula (), Y is -CH=CH- or -C≡C-, R is a phenyl group, and R1 is an aliphatic group which may have a substituent inert to tert-butoxypotassium. A hydrocarbon group, R 2 is hydrogen or a group defined similarly to R 1 , R 3 is hydrogen or a tetrahydropyranyloxy group, R 4 is an acetyl group or a tetrahydropyranyl group, and n is 0 or a positive integer. The present invention is represented by the following reaction formula. As shown in the above formula (), the present invention can be said to be a synthetic method in which the conjugated chain of the unsaturated bond in the carbon skeleton of the sulfone starting material is extended by two places. For example, n=0
In the case of , a diene compound is produced, and in the case of n=1, when Y is a double bond, the product is a triene compound, and when Y is a triple bond, an ene-yn-ene compound is produced. Furthermore, a major feature of the present invention is that the double bond produced has an extremely high production rate of the trans isomer, and some compounds show a substantially 100% trans isomer production rate. In the present invention, β used as a starting material
Sulfones having a protected hydroxy group at the - position can be easily synthesized, for example, by adding a compound having a suitable sulfonyl group and an aldehyde, as shown in the following formula (). According to the formula (), a suitable sulfone is anionized with, for example, n-butylated lithium (n-BuLi) and reacted with an aldehyde, and the resulting hydroxy compound is anionized with, for example, acetic anhydride (Ac 2 O). A protecting group (acetyl group) can be introduced into the hydroxyl group by a conventional method involving the action of +pyridine (Py). As the protecting group, an acetyl group and a tetrahydropyranyl group, which are commonly used in organic synthesis reactions, are used. The polyene-forming reaction of the present invention is an elimination reaction between a sulfonyl group and a β-hydroxy group, as shown in the above formula (), and the reaction is extremely easy. That is, the object is achieved by treating the starting material sulfone with potassium tert-butoxy using tetrahydrofuran or a mixture of tetrahydrofuran-tert-butanol as a solvent. In this case, the starting material compound of formula () is a fatty acid which may have a substituent that does not interact with tert-butoxypotassium in which R 1 is a strong alkali, such as an ethylenedioxy group or a tetrahydropyranyloxy group. It must be a compound in which R 2 is hydrogen or an aliphatic hydrocarbon group similar to R 1 above. Potassium tert-butoxy is used in an amount equivalent to or more, usually about 2.5 to 15 moles, per mole of sulfone.
A reaction temperature of room temperature to reflux temperature is sufficient, and the reaction time varies depending on the sulfone used and is not particularly limited. (Example) Examples 1 to 7 Using the starting materials shown in Table 1, corresponding conjugated unsaturated compounds were produced. In the table, the molar ratio of t-BuOK (potassium tert-butoxy) is expressed as t-BuOK/starting material. Product yields are values obtained by column chromatography purification. In addition, THF is tetrahydrofuran, t-
BuOH represents tertiary butanol, THP represents a tetrahydropyranyl group, Ph represents a phenyl group, Ac represents an acetyl group, and Me represents a methyl group.
【表】【table】
【表】
実施例1〜7の生成物の核磁気共鳴スペクトル
は次のとおりであつた。
実施例1:1H NMR(CCl4)δ0.76−1.13(m、
3H、CH3)、1.00(d、6H、C(CH3)2、J=
6.8Hz、1.27−1.70(m、8H、CH2)、1.76−2.61
(m、3H、CH2C=C、CHC=C)、4.86−6.36
(m、4H、CH=CH).13 C NMR(CDCl3)
δ122.6、127.4、128.7、130.3、132.6、139.3、
141.5(olefinic carbons).
実施例2:1H NMR(CCl4)δ0.80(t、3H、
CH3、J=4Hz)、1.00−1.50(m、10H、
CH2)、1.50−2.20(m、2H、CH2C=C)、4.60
−6.40(m、5H、C=CH2、C=CH)、13 C
NMR(CDCl3)δ114.5、130.9、135.6、137.4
(olefinic carbons).
実施例3:1H NMR(CCl4)δ1.00(d、6H、C
(CH3)2、J=6.8Hz)、1.34(s、1.80H、CH3)、
1.41(s、1.20H、CH3)、2.00−2.60(m、1H、
CHC=C)、3.80(s、4H、OCH2CH2O)、
5.00−7.00(m、4H、CH=CH)
実施例4:1H NMR(CCl4)δ0.79(t、3H、
CH3、J=4Hz)、0.95−1.70(m、14H、
CH2)、1.80(s、6H、CH3)、2.42(t、2H、
CH2CO、J=7Hz)、5.80(d、1H、C=CHC
=CCO、J=12Hz)、5.90(d、1H、C=
CHCO、J=15Hz)、7.27(dd、1H、CH=
CCO、J=15、12Hz).
実施例5:1H NMR(CCl4)δ1.00(d、6H、C
(CH3)2、J=6Hz)、0.70−1.00(m、3H、
CH3)、1.11−1.59(m、4H、CH2)、1.80−2.60
(m、3H、CHC=C、CH2C=C)5.00−6.40
(m、6H、CH=CH)
実施例6:1H NMR(CCl4)δ1.50(s、3H、
CH3)、1.58(s、3H、CH3)、1.68(s、6H、
CH3、)、1.79(s、3H、CH3)、1.90−2.20(m、
4H、CH2、C=C)、4.70−5.15(m、1H、C
=CH)、5.58−6.60(m、7H、C=CH).
実施例7:1H NMR(CCl4)δ0.70−1.05(m、
3H、CH3)、0.94(d、6H、C(CH3)2、J=
6.8Hz)、1.07−1.63(m、8H、CH2)、2.00−
2.45(m、3H、CHC=C、CH2C=C)、5.11−
6.57(m、4H、CH=CH).[Table] The nuclear magnetic resonance spectra of the products of Examples 1 to 7 were as follows. Example 1: 1 H NMR (CCl 4 ) δ0.76−1.13 (m,
3H, CH 3 ), 1.00(d, 6H, C(CH 3 ) 2 , J=
6.8Hz, 1.27-1.70 (m, 8H, CH2 ), 1.76-2.61
(m, 3H, CH2C =C, CHC=C), 4.86−6.36
(m, 4H, CH=CH). 13C NMR ( CDCl3 )
δ122.6, 127.4, 128.7, 130.3, 132.6, 139.3,
141.5 (olefinic carbons). Example 2: 1 H NMR (CCl 4 ) δ0.80 (t, 3H,
CH3 , J=4Hz), 1.00-1.50(m, 10H,
CH 2 ), 1.50−2.20 (m, 2H, CH 2 C=C), 4.60
-6.40 (m, 5H, C=CH 2 , C=CH), 13C
NMR ( CDCl3 ) δ114.5, 130.9, 135.6, 137.4
(olefinic carbons). Example 3: 1 H NMR (CCl 4 ) δ1.00 (d, 6H, C
( CH3 ) 2 , J=6.8Hz), 1.34(s, 1.80H, CH3 ),
1.41 (s, 1.20H, CH 3 ), 2.00−2.60 (m, 1H,
CHC=C), 3.80 (s, 4H, OCH 2 CH 2 O),
5.00−7.00 (m, 4H, CH=CH) Example 4: 1 H NMR (CCl 4 ) δ0.79 (t, 3H,
CH3 , J=4Hz), 0.95-1.70(m, 14H,
CH 2 ), 1.80 (s, 6H, CH 3 ), 2.42 (t, 2H,
CH 2 CO, J = 7Hz), 5.80 (d, 1H, C = CHC
= CCO, J = 12Hz), 5.90 (d, 1H, C =
CHCO, J=15Hz), 7.27(dd, 1H, CH=
CCO, J=15, 12Hz). Example 5: 1 H NMR (CCl 4 ) δ1.00 (d, 6H, C
( CH3 ) 2 , J=6Hz), 0.70−1.00(m, 3H,
CH3 ), 1.11-1.59 (m, 4H, CH2 ), 1.80-2.60
(m, 3H, CHC=C, CH2C =C) 5.00−6.40
(m, 6H, CH=CH) Example 6: 1 H NMR (CCl 4 ) δ1.50 (s, 3H,
CH 3 ), 1.58 (s, 3H, CH 3 ), 1.68 (s, 6H,
CH 3 , ), 1.79 (s, 3H, CH 3 ), 1.90−2.20 (m,
4H, CH 2 , C=C), 4.70-5.15 (m, 1H, C
= CH), 5.58-6.60 (m, 7H, C=CH). Example 7: 1 H NMR (CCl 4 ) δ0.70−1.05 (m,
3H, CH 3 ), 0.94(d, 6H, C(CH 3 ) 2 , J=
6.8Hz), 1.07-1.63 (m, 8H, CH2 ), 2.00-
2.45 (m, 3H, CHC=C, CH2C =C), 5.11−
6.57 (m, 4H, CH=CH).
Claims (1)
ヒドロキシ基を有する下記一般式()で表わさ
れるスルホン類を第三ブトキシカリウムで処理す
ることを特徴とする共役不飽和化合物の製法。 但し、()式において、Yは−CH=CH−又
は−C≡C−、Rはフエニル基、R1は第三ブト
キシカリウムに対して不活性な置換基を有してい
てもよい脂肪族炭化水素基、R2は水素又はR1と
同様に定義される基、R3は水素又はテトラヒド
ロピラニルオキシ基、R4はアセチル基又はテト
ラヒドロピラニル基、nは0又は正整数である。[Claims] 1. A conjugated unsaturated compound characterized in that a sulfone represented by the following general formula () having a protected hydroxy group at the β position relative to a sulfonyl group is treated with potassium tert-butoxy. manufacturing method. However, in formula (), Y is -CH=CH- or -C≡C-, R is a phenyl group, and R1 is an aliphatic group which may have a substituent inert to tert-butoxypotassium. A hydrocarbon group, R 2 is hydrogen or a group defined similarly to R 1 , R 3 is hydrogen or a tetrahydropyranyloxy group, R 4 is an acetyl group or a tetrahydropyranyl group, and n is 0 or a positive integer.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP59110231A JPS60252431A (en) | 1984-05-29 | 1984-05-29 | Production of conjugated unsaturated compound |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP59110231A JPS60252431A (en) | 1984-05-29 | 1984-05-29 | Production of conjugated unsaturated compound |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS60252431A JPS60252431A (en) | 1985-12-13 |
JPH0355451B2 true JPH0355451B2 (en) | 1991-08-23 |
Family
ID=14530417
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP59110231A Granted JPS60252431A (en) | 1984-05-29 | 1984-05-29 | Production of conjugated unsaturated compound |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS60252431A (en) |
-
1984
- 1984-05-29 JP JP59110231A patent/JPS60252431A/en active Granted
Also Published As
Publication number | Publication date |
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JPS60252431A (en) | 1985-12-13 |
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