GB824175A - Reactions involving grignard reagents - Google Patents
Reactions involving grignard reagentsInfo
- Publication number
- GB824175A GB824175A GB3657/56A GB365756A GB824175A GB 824175 A GB824175 A GB 824175A GB 3657/56 A GB3657/56 A GB 3657/56A GB 365756 A GB365756 A GB 365756A GB 824175 A GB824175 A GB 824175A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- aryl
- substituents
- substituted
- ring
- 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
Links
- 238000006243 chemical reaction Methods 0.000 title 1
- 150000004795 grignard reagents Chemical class 0.000 title 1
- -1 heterocyclic radical Chemical class 0.000 abstract 33
- 125000003118 aryl group Chemical group 0.000 abstract 12
- 125000001424 substituent group Chemical group 0.000 abstract 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
- 229910052799 carbon Inorganic materials 0.000 abstract 4
- 150000002576 ketones Chemical class 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 abstract 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 125000003342 alkenyl group Chemical group 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- 125000004429 atom Chemical group 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 3
- 150000002430 hydrocarbons Chemical group 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- 238000002360 preparation method Methods 0.000 abstract 3
- 125000001544 thienyl group Chemical group 0.000 abstract 3
- VUFKMYLDDDNUJS-UHFFFAOYSA-N 2-(ethoxymethyl)oxolane Chemical compound CCOCC1CCCO1 VUFKMYLDDDNUJS-UHFFFAOYSA-N 0.000 abstract 2
- BTHLKLUTMYTDFM-UHFFFAOYSA-N 2-ethoxyoxane Chemical compound CCOC1CCCCO1 BTHLKLUTMYTDFM-UHFFFAOYSA-N 0.000 abstract 2
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 abstract 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 abstract 2
- UURIMXSRDJGGFO-UHFFFAOYSA-N 4-chloropyrimidine-2-carboxylic acid Chemical compound OC(=O)C1=NC=CC(Cl)=N1 UURIMXSRDJGGFO-UHFFFAOYSA-N 0.000 abstract 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 abstract 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 abstract 2
- 150000005840 aryl radicals Chemical class 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 125000002734 organomagnesium group Chemical group 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 abstract 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 abstract 2
- 125000004076 pyridyl group Chemical group 0.000 abstract 2
- 239000011541 reaction mixture Substances 0.000 abstract 2
- 125000002348 vinylic group Chemical group 0.000 abstract 2
- FGYBDASKYMSNCX-UHFFFAOYSA-N 2,5-dichlorothiophene Chemical compound ClC1=CC=C(Cl)S1 FGYBDASKYMSNCX-UHFFFAOYSA-N 0.000 abstract 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 abstract 1
- 239000005711 Benzoic acid Substances 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- IJCVBMSXIPFVLH-UHFFFAOYSA-N [C].S=O Chemical compound [C].S=O IJCVBMSXIPFVLH-UHFFFAOYSA-N 0.000 abstract 1
- RTROMBRPVSMXST-UHFFFAOYSA-M [Cl-].ClC=1SC(=CC1)[Mg+] Chemical class [Cl-].ClC=1SC(=CC1)[Mg+] RTROMBRPVSMXST-UHFFFAOYSA-M 0.000 abstract 1
- CWRYPZZKDGJXCA-UHFFFAOYSA-N acenaphthene Chemical compound C1=CC(CC2)=C3C2=CC=CC3=C1 CWRYPZZKDGJXCA-UHFFFAOYSA-N 0.000 abstract 1
- 150000001253 acrylic acids Chemical class 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000005336 allyloxy group Chemical group 0.000 abstract 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 abstract 1
- 125000000732 arylene group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 abstract 1
- 235000010233 benzoic acid Nutrition 0.000 abstract 1
- 150000001559 benzoic acids Chemical class 0.000 abstract 1
- 239000012965 benzophenone Substances 0.000 abstract 1
- 150000008366 benzophenones Chemical class 0.000 abstract 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 abstract 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 125000006267 biphenyl group Chemical group 0.000 abstract 1
- 229910002092 carbon dioxide Inorganic materials 0.000 abstract 1
- 239000001569 carbon dioxide Substances 0.000 abstract 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 abstract 1
- SKOLWUPSYHWYAM-UHFFFAOYSA-N carbonodithioic O,S-acid Chemical compound SC(S)=O SKOLWUPSYHWYAM-UHFFFAOYSA-N 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 150000008422 chlorobenzenes Chemical class 0.000 abstract 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 abstract 1
- 150000004292 cyclic ethers Chemical class 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 abstract 1
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 abstract 1
- 125000005509 dibenzothiophenyl group Chemical group 0.000 abstract 1
- 150000005690 diesters Chemical class 0.000 abstract 1
- 125000004119 disulfanediyl group Chemical group *SS* 0.000 abstract 1
- VLQLCEXNNGQELL-UHFFFAOYSA-N ethyl 1,3-benzothiazole-2-carboxylate Chemical compound C1=CC=C2SC(C(=O)OCC)=NC2=C1 VLQLCEXNNGQELL-UHFFFAOYSA-N 0.000 abstract 1
- CWJRNKXXSWYYTJ-UHFFFAOYSA-N ethyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OCC)=NC2=C1 CWJRNKXXSWYYTJ-UHFFFAOYSA-N 0.000 abstract 1
- BMOKMXXTOZFEIZ-UHFFFAOYSA-N ethyl 5-chlorothiophene-2-carboxylate Chemical compound CCOC(=O)C1=CC=C(Cl)S1 BMOKMXXTOZFEIZ-UHFFFAOYSA-N 0.000 abstract 1
- UOOVXLMQDPLECA-UHFFFAOYSA-N ethyl 6-chloro-2-methoxyacridine-9-carboxylate Chemical compound ClC=1C=C2N=C3C=CC(=CC3=C(C2=CC1)C(=O)OCC)OC UOOVXLMQDPLECA-UHFFFAOYSA-N 0.000 abstract 1
- JZGZKRJVTIRPOK-UHFFFAOYSA-N ethyl thiophene-2-carboxylate Chemical compound CCOC(=O)C1=CC=CS1 JZGZKRJVTIRPOK-UHFFFAOYSA-N 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 125000000524 functional group Chemical group 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000002883 imidazolyl group Chemical group 0.000 abstract 1
- 125000001041 indolyl group Chemical group 0.000 abstract 1
- 239000011777 magnesium Substances 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L magnesium chloride Substances [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 abstract 1
- 229910001629 magnesium chloride Inorganic materials 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 abstract 1
- 125000005561 phenanthryl group Chemical group 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 1
- GQONLASZRVFGHI-UHFFFAOYSA-M phenylmagnesium chloride Chemical class Cl[Mg]C1=CC=CC=C1 GQONLASZRVFGHI-UHFFFAOYSA-M 0.000 abstract 1
- 125000001388 picenyl group Chemical group C1(=CC=CC2=CC=C3C4=CC=C5C=CC=CC5=C4C=CC3=C21)* 0.000 abstract 1
- 125000002098 pyridazinyl group Chemical group 0.000 abstract 1
- 125000000714 pyrimidinyl group Chemical group 0.000 abstract 1
- 125000004151 quinonyl group Chemical group 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 125000006413 ring segment Chemical group 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- 125000003944 tolyl group Chemical group 0.000 abstract 1
- 125000004306 triazinyl group Chemical group 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
- 125000005023 xylyl group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/02—Magnesium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
A process for the preparation of an alcohol, an organic acid, an ester, a ketone, a thio ketone or an organic thio acid comprises reacting with a chlorocarbonic ester, a diester of carbonic acid, carbon dioxide, carbon disulphide or carbon oxysulphide an organo-magnesium chloride complex of the formula R(MgCl)x.nQ and, where necessary, hydrolysing the reaction mixture, R being a substituted or unsubstituted aryl or arylene group, a substituted or unsubstituted vinylic group or a substituted or unsubstituted heterocyclic radical which exhibits aromatic or pseudo aromatic characteristics and which includes in its heterocyclic ring an oxygen, sulphur or tertiary nitrogen atom and is bound to magnesium through a carbon atom of the aromatic or pseudo aromatic ring and R containing no functional group which is reactive under the conditions for the formation of the complex, Q being a molecule of a substituted or unsubstituted heterocyclic ether having 5 or 6 atoms in the ring, of which atoms only one is oxygen, the other ring atoms being carbon with the exception that a substituted nitrogen atom may replace the carbon atom in the 4position when the ring has 6 atoms, the ring containing not more than one double bond and at least one carbon atom in the ring adjacent the oxygen atom being free of any substituents, said ether containing no substituent which reacts with an organomagnesium chloride complex or with the other components or products of the reaction mixture, x being 1 or 2 and n being a small whole number of the order of 1 to 3. Cyclic ethers specified include tetrahydrofuran, tetrahydropyran. 2-methyltetrahydrofuran, 2-ethoxytetrahydropyran, tetrahydrofurfuryl ethyl ether, dihydropyran and N-methyl morpholine which may contain as substituents alkyl, aryl, alkoxy and aryloxy groups. Representative of the aryl radicals in the aryl magnesium chloride complexes specified are phenyl, any of the hydrogen atoms of which may be replaced by chlorine, alkyl, aryl, alkoxy or aryloxy radicals which optionally may be substituted with alkenyl, aralkyl, thienyl, thenyl and furyl radicals, allyloxy and dialkylamino radicals, two or more adjacent hydrocarbon substituents optionally being linked to form a cyclic saturated or condensed aromatic ring. The aryl radicals may be polynuclear, e.g. as in anthracyl, polychlorobiphenyl and acenaphthalenyl. Additional substituents mentioned include fluorine and alkylidenedioxy radicals. Representative of the arylene radicals in the arylene di-magnesium chloride complexes specified are those derived from benzene, diphenyl, anthracene and phenanthrene which may bear substituents specified above as aryl substituents. Representative of the heterocyclic radicals in the heterocyclic magnesium chloride complexes specified are thiophenyl, benzothiophenyl and dibenzothiophenyl, wherein nuclear hydrogen may be replaced by chlorine or condensed rings or additional substituents specified above as aryl substituents, pyridyl, quinonyl, acridyl, furyl, N-substituted pyrryl, indolyl, benzofuryl, dibenzofuryl, imidazolyl, benzoxazolyl, pyrimidyl, triazinyl, and pyridazinyl. Representative of vinylic groups in the vinylic magnesium chloride complexes specified are those in which any of the hydrogen atoms of the vinyl group are replaced by aliphatic or aromatic hydrocarbon groups or by two substituents forming a ring, e.g. as in cyclohexenyl. Specific products of the process mentioned include benzoic acid, p-toluic acid, the corresponding chloro acids and carboxylic acid derivatives of various polynuclear hydrocarbons, e.g. chrysene and acenaphthene, acrylic acid and substituted acrylic acids, e.g. isobutene-1-oic and p-methoxy styrene-a -carboxylic acid, terephthalic acid, polychlorinated benzoic acids, benzophenones, symmetrical ketones derived from various polynuclear hydrocarbons, Michler's ketone, ethyl 2-thienylcarboxylate, a -pyridyl dithionic acid, bis-2quinonyl ketone, 6-quinonyl-8-quinonyl ketone, ethyl 2 - benzoxazolyl carboxylate, ethyl 2 - benzothiazolyl carboxylate, chloropyrimidinylcarboxylic acid, ethyl 6-chloro-2-methoxyacrid-9-yl carboxylate, chloropyrimidinyl carboxylic acid, dithio furoic acid, a polythiophenylene ketone, ethyl 5-chlorothiophenoate and dithioacrylic acid. Chlorocarbonic esters specified for use in the process include alkyl, aryl, alkenyl, aralkyl and alkaryl chlorocarbonates. Carbonates specified include alkyl, aryl, alkenyl, aralkyl and alkaryl diesters of carbonic acid. Organomagnesium chloride complexes, the preparations of which are described, include tetrahydrofuran complexes with phenyl-, vinyl-, m- and p - chlorophenyl-, tolyl-, xenyl-, terphenyl-, naphthyl-, anthracyl-, phenanthryl-, xylyl-, phenylnaphthyl-, anisyl-, phenethyl-, pyrenyl-, cadalenyl-, perylenyl-, acenaphthyl-, chrysenyl-, picenyl-, chlortolyl-, thienyl-, a pyridyl-, 2-quinonyl-, 6- and 8-quinonyl-, 2benzoxazolyl-, 2 - benzothiazolyl-, 2 - methyl - benzothiazolyl-, 6 - chloro - 2 - methoxy - acrid9-yl-, chloropyrimidyl-, and 2-chloro-5-thiophenyl magnesium chlorides and with organomagnesium chlorides derived from chlorobenzenes containing 3-6 chlorine atoms, pdichlorobenzene and 2,5-dichlorothiophene. The preparation of phenyl magnesium chloride complexes in the presence of tetrahydropyran, 2methyltetrahydrofuran, 2 - ethoxymethyltetrahydrofuran and 2-ethoxytetrahydropyran is mentioned. Specifications 776,993, 777,158 and 779,100 are referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US824175XA | 1955-02-21 | 1955-02-21 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB824175A true GB824175A (en) | 1959-11-25 |
Family
ID=22171080
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3657/56A Expired GB824175A (en) | 1955-02-21 | 1956-02-06 | Reactions involving grignard reagents |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB824175A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2251242A (en) * | 1990-12-31 | 1992-07-01 | Robert Ramage | Protective group |
US7091360B2 (en) | 2002-04-16 | 2006-08-15 | Aventis Pharma S.A. | Process for preparing heteroaryl and unsaturated heterocycloalkylmagnesium reagents and uses thereof |
CN107445939A (en) * | 2017-09-18 | 2017-12-08 | 张家港九力新材料科技有限公司 | A kind of preparation method of the dicarboxylic acids of fine work thiophene 2,5 |
CN110028610A (en) * | 2019-04-02 | 2019-07-19 | 天津南开和成科技有限公司 | A kind of solid macromolecule Grignard Reagent and preparation method thereof |
-
1956
- 1956-02-06 GB GB3657/56A patent/GB824175A/en not_active Expired
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2251242A (en) * | 1990-12-31 | 1992-07-01 | Robert Ramage | Protective group |
GB2251242B (en) * | 1990-12-31 | 1995-01-11 | Robert Ramage | Protecting compound |
US7091360B2 (en) | 2002-04-16 | 2006-08-15 | Aventis Pharma S.A. | Process for preparing heteroaryl and unsaturated heterocycloalkylmagnesium reagents and uses thereof |
CN107445939A (en) * | 2017-09-18 | 2017-12-08 | 张家港九力新材料科技有限公司 | A kind of preparation method of the dicarboxylic acids of fine work thiophene 2,5 |
CN110028610A (en) * | 2019-04-02 | 2019-07-19 | 天津南开和成科技有限公司 | A kind of solid macromolecule Grignard Reagent and preparation method thereof |
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