GB2088398A - 1,2-Bis(trialkylsiloxymethyl)- cyclopropanes and a Method for Preparing 1,2-Bis(trialkylsiloxy- methyl)cyclopropanes - Google Patents
1,2-Bis(trialkylsiloxymethyl)- cyclopropanes and a Method for Preparing 1,2-Bis(trialkylsiloxy- methyl)cyclopropanes Download PDFInfo
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- GB2088398A GB2088398A GB8038796A GB8038796A GB2088398A GB 2088398 A GB2088398 A GB 2088398A GB 8038796 A GB8038796 A GB 8038796A GB 8038796 A GB8038796 A GB 8038796A GB 2088398 A GB2088398 A GB 2088398A
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- cyclopropanes
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- 238000000034 method Methods 0.000 title claims description 10
- 150000001942 cyclopropanes Chemical class 0.000 title abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- SWXDNKVUVKMURJ-UHFFFAOYSA-N [2-(hydroxymethyl)cyclopropyl]methanol Chemical class OCC1CC1CO SWXDNKVUVKMURJ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract 2
- 125000003118 aryl group Chemical group 0.000 claims abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- -1 bicyclic amines Chemical class 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 238000005822 methylenation reaction Methods 0.000 claims description 2
- 229950011148 cyclopropane Drugs 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000007858 starting material Substances 0.000 abstract description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 14
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 229960004132 diethyl ether Drugs 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 229910052742 iron Inorganic materials 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000000370 acceptor Substances 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- WSSDGZWSPMAECX-UHFFFAOYSA-N 2-azabicyclo[3.1.0]hexane Chemical compound C1CNC2CC21 WSSDGZWSPMAECX-UHFFFAOYSA-N 0.000 description 1
- HGWUUOXXAIISDB-UHFFFAOYSA-N 3-azabicyclo[3.1.0]hexane Chemical compound C1NCC2CC21 HGWUUOXXAIISDB-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GSOLWAFGMNOBSY-UHFFFAOYSA-N cobalt Chemical compound [Co][Co][Co][Co][Co][Co][Co][Co] GSOLWAFGMNOBSY-UHFFFAOYSA-N 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229940052303 ethers for general anesthesia Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 1
- 229940071536 silver acetate Drugs 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/128—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by alcoholysis
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/09—Geometrical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1,2-Bis(trialkylsiloxymethyl)cyclo- propanes according to the general formula <IMAGE> wherein R<1>, R<2>, R<3> and R<4> may be the same or different and are H or alkyl, and each R<5> which may be the same or different is alkyl, aryl, alkaryl or aralkyl, are novel compounds. They are suitable starting materials for otherwise difficult to prepare 1,2- bis(hydroxymethyl)cyclopropanes, the cis-isomers thereof being of particular interest in that they can be converted into 3-azabicyclo[3.1.0]hexane-type compounds by cycloamination.
Description
SPECIFICATION 1 ,2-bis(trialkylsiloxymethyl)cyclopropanes and a Method for Preparing 1,2 bis(trialkylsiloxymethyl)cyclopropanes The present invention relates to novel 1,2bis(trialkylsiloxymethyl)cyclopropanes as well as to a method of preparing 1,2-bis(trialkylsiloxy- methyl)cyclopropanes, The compounds according to the present invention are of interest as intermediates in the preparation of the corresponding 1 ,2-bis(hydroxymethyl)cyclopropanes which are otherwise difficult to prepare but which are valuable starting materials for chemical processes involving ring-closure.
The present invention thus relates to compounds according to the general formula
wherein R1 and R2, which may be the same or different, each represent a hydrogen atom or a lower alkyl group; R3 and R4, which may the same or different, each represent a hydrogen atom or an alkyl group and the groups R5, which may be the same or different, each represent an alkyl, aryl alkaryl or aralkyl group.
Preferred compounds according to the general formula I are those wherein R1, R2, R3 and R4 each represent a hydrogen atom and the groups R5, which may be the same or different, each represent an alkyl group having up to 4 carbon atoms. The present invention relates in particular to the compound 1 ,2-bis(trimethylsiloxymethyl)cyclopropane. It will be appreciated that the compounds according to the general formula I may exhibit geometrical as well as optical isomerism. The individual isomers as well as mixtures thereof are within the scope of the present invention.
The present invention also relates to a method for preparing compounds according to the general formula I which comprises reacting a compound according to the general formula
wherein R3, R4 and R5 are as defined hereinbefore with a compound according to the general formula CRIR2Hal2, wherein R' represents a hydrogen atom or an alkyl group and R2 represents a hydrogen atom and Hal represents a bromine or iodine moiety in the presence of a halide-acceptor. Suitable halide-acceptors comprise heavy metals and/or noble metals such as Zn/Cu and Zn/Ag-combinations. Good results can be obtained using diiodomethane as the active compound in a Simmons-Smith-type reaction.Normally the methylenation will be carried out conveniently at temperatures up to 1 000C, preferably in the range of from 100C to 400 C. The reaction can be carried out conveniently in the presence of an inert soivent such as an aliphatic ether, e.g. diethylether, tetrahydrofuran and dioxane. Good results have been obtained using diethylether.
The compounds according to the general formula II can be prepared conveniently by silylating the corresponding 1,2-bis(hydroxymethyl) compounds according to the general formula
wherein R3 and R4 are as defined hereinbefore with a silylating agent according to the general formula (R6)3SiX wherein each group R5, which may be the same or different, is as defined hereinbefore and X represents a halogen atom, especially a chlorine or bromine atom. Preferably, the reaction is carried out in the presence of an acid scavenger such as a tertiary amine, e.g.
triethylamine or pyridine. Good results have been obtained using a trialkylsilyl halide as the silylating agent: a quantitative yield was obtained in the reaction between 1 ,4-dihydroxy-butene-2 and trimethylsilyl chloride. The reaction can be performed at moderate temperatures, e.g.
temperatures up to 500C can be used advantageously. The reaction can be carried out in the presence or in the absence of a solvent.
Examples of suitable solvents comprise ethers such as diethylether as well as cyclic ethers, e.g.
tetrahydrofuran and dioxane.
The present invention relates in particular to a process for preparing compounds according to the general formula I by reacting a compound according to the general formula II, which has been preferably obtained by reacting a compound according to the general formula II with a compound according to the general formula (R5)3SiX (wherein R5 and X are as defined hereinbefore), with a compound according to the general formula CR'R2Hal2 wherein R1, R2 and Hal are as defined hereinbefore.
The novel compounds according to the present invention can be used as starting materials for many chemical reactions. For instance, they can be converted into the corresponding 1,2bis(hydroxymethyl)cyclopropanes by reacting them with an alkanol, in particular a lower alkanol such as methanol or ethanol. Normally, the alcoholysis is carried out at ambient or moderate temperatures, e.g. temperatures up to the boiling point of the alkanol applied can be suitably used.
It should be noted that 1 ,2-bis(hydroxymethyl)cyciopropanes are difficult to prepare otherwise.
The 1 ,2-bis(hydroxymethyl)cyclopropanes obtained can be converted into a number of products by various chemical reactions. One of the most interesting reactions comprises the socalled cycloamination reaction which affords starting from cis-compounds the appropriate bicyclic amines which are of interest as precursors for 3-azabicycio[3.1 .0]hexane-2- carboxylic acids and esters which are active as pollen suppressants.
A suitable cycioamination reaction comprises reacting a 1 ,2-bis(hydroxymethyl)cyclopropane compound with ammonia at elevated temperature in the presence of a catalyst comprising at least two group VIII metals.
Examples of Group VIII metal combinations are iron/cobalt and iron/nickel. Preferably, the cycloamination is carried out in the presence of hydrogen at a reaction temperature of between 1 500C and 3000C, most preferably between 1 500C and 2000C. The reaction is carried out at higher pressures, e.g. pressures up to 100 bar can be suitably used as well as even higher pressures.
Good results have been obtained using pressures of 30 bar and more.
Although the two metals in the catalyst can be used in equal atomic ratios, it is preferred to use a rather low amount of iron in the catalyst, e.g. in an amount of 10%w or even less, calculated on the other Group VIII metal present. It will be appreciated that not only 1,2-bis(hydroxymethyl)cyclopropanes but also other suitable diols such as diethylene glycol and butane-diol-2,3 as well as dialkanolamines can be converted into the corresponding cyclic (di)amines. It is also possible to have additional Group VIII metal compounds, e.g. small amounts of platinum and/or iridium present in the catalytic system.
The invention will now be illustrated by means of the following Example.
Example a. Preparation of cis-1 ,4bis(trimethylsiloxy- methyl)but-2-ene
To a mixture of cis-1 ,4-dihydroxybut-2-ene (10g; 0.11 mole) and triethylamine (33g; 0.33 mole) in diethylether (500ml) were added 359 of trimethylsilyl chloride over a period of 30 minutes at room temperature. The reaction mixture was then filtered to remove the triethylamine
hydrochloric acid salt. After evaporation of the solvent cis- Q-bis(tri 1,4-bis(trimethylsiloxymethyl)but-2- ene was obtained in 80% yield (23.39).
b. Preparation of cis-1 ,2-bis(trimethylsiloxy- methyl)cyclopropane
Zinc pellets (179; 0.26 mole) were added at
once to a hot solution of silveracetate (100mg) in
acetic acid under vigourous stirring. Thereafter the mixture was decanted and washed with small
portions of diethyiether (5 times). To the Zn/Ag
couple thus prepared diethylether was added
(150ml) and thereafter diiodomethane (429; 0.2
mole) and cis-1 ,4-bis(trimethylsiloxymethyl)but- 2-ene (23g; 0.1 mole) were added dropwise. The
mixture thus obtained was kept under reflux for
20 hours. Thereafter no starting material could be
detected any more.The reaction mixture was
worked up by adding slowly pyridine, filtration
and evaporation of dimethylether. 1,2- Bis(trimethylsiloxymethyl)cyclopropane had been obtained in 65% yield (20g; purity 80%). The compound has a boiling point of 100 1 020C/1 4mm and its structure was confirmed by
NMR-analysis. The z-values (relative to TMS) were: 6.2-6.4 broad doublet (4H); 8.5-8.85 multiplet (2H); 8.9-9.2 multiplet (1 H) and 9.9 broad singlet (1 9H).
c. Preparation of cis-1 ,2-bis(hydroxy- methyl)cyclopropane
In order to illustrate the versatility of the 1,2bis(trialkylsiloxymethyl)cyclopropanes according to the present invention, 1 ,2-bis(trimethylsiloxymethyl)cyclopropane (20g) was heated in methanol (80ml) under reflux during 12 hours without any catalyst present. 95% of the starting material had been converted into cis-1,2- bis(hydroxymethyl)cyclopropane. The product was checked with an authentic sample of cis-1,2- bis(hydroxymethyl)cyclopropane.The cis-1,2bis(hydroxymethyl)cyclopropane thus obtained can be suitably converted into 2-aza bicyclo[3.1 .0]hexane by pumping a 10%w solution of this compound in tetrahydrofuran at a rate of 1 Oml/h (LSHV 0.1) through a tube over a nickel catalyst containing also iron (5%w on nickel and optionally a small amount of platinum (e.g. 0.2%w) together with a five-fold excess of ammonia in the presence of hydrogen. The total pressure amounted to 40 bar at the reaction temperature of 1 500C. No starting material could be found (GLC-analysis) and 3-aza bicyclo[3.1 .0]hexane was the only product isolated in a yield of 65% which presumably was even higher due to the relative volatility of the product. No polymeric material could be detected whilst the catalyst remained active.
Claims (9)
1. Compounds according to the general formula
wherein R' and R2 which may be the same or different each represent a hydrogen atom or a lower alkyl group; R3 and R4 which may be the same or different each represent a hydrogen atom or an alkyl group and the groups R5 which may be the same or different each represent an alkyl, aryl, alkaryl or aralkyl group.
2. Compounds according to claim 1, wherein
R1, R2, Era and R4 each represent a hydrogen atom and the groups R5 which may be the same or different each represent an alkyl group having up to 4 carbon atoms.
3. 1,2-Bis(tri methylsiioxym ethyl)cyclo- propane.
4. Process for the preparation of compounds according to any of claims 1-3, which comprises reacting a compound according to the general formula
wherein R3, R4 and R5 are as defined hereinbefore with a compound according to the general formula CR'R2Hal2, wherein R1 represents a hydrogen atom or an alkyl group and R2 represents a hydrogen atom and Hal represents a bromine or iodine moiety in the presence of a halide-acceptor.
5. Process according to claim 4, wherein the methylenation reaction is carried out at a temperature of up to 1000C, preferably at a temperature between 100C and 400C, using diiodomethane as the active compound.
6. Process according to claim 4 or 5, which
comprises reacting a compound according to the
general formula II, which has been obtained by silylating a 1 ,2-bis(hydroxymethyl) compound
according to the general formula
wherein R3 and R4 are as defined hereinbefore with a compound according to the general formula (R5)3SiX, wherein each group R5-which may be the same or different-is as defined hereinbefore and X represents a halogen atom, with a compound according to the general formula CRlR2Hal2 wherein R', R2 and Hal are as defined hereinbefore.
7. Process for the preparation of 1,2bis(hydroxymethyl)cyclopropanes which comprises reacting a compound according to any one of claims 1-3, with an alkanol, in particular a lower alkanol and optionaily converting the 1,2bis(hydroxymethyl)cyclopropanes into the corresponding bicyclic amines via cycloamination.
8. Process according to any one of claims 4 7, substantially as hereinbefore described with particular reference to the Example.
9. Compounds according to any one of claims 1-3, whenever prepared by a process as claimed in any one of claims 4 6.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8038796A GB2088398A (en) | 1980-12-03 | 1980-12-03 | 1,2-Bis(trialkylsiloxymethyl)- cyclopropanes and a Method for Preparing 1,2-Bis(trialkylsiloxy- methyl)cyclopropanes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8038796A GB2088398A (en) | 1980-12-03 | 1980-12-03 | 1,2-Bis(trialkylsiloxymethyl)- cyclopropanes and a Method for Preparing 1,2-Bis(trialkylsiloxy- methyl)cyclopropanes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB2088398A true GB2088398A (en) | 1982-06-09 |
Family
ID=10517742
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8038796A Withdrawn GB2088398A (en) | 1980-12-03 | 1980-12-03 | 1,2-Bis(trialkylsiloxymethyl)- cyclopropanes and a Method for Preparing 1,2-Bis(trialkylsiloxy- methyl)cyclopropanes |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2088398A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4535174A (en) * | 1984-11-02 | 1985-08-13 | General Electric Company | Free-radical initiators and method for making |
-
1980
- 1980-12-03 GB GB8038796A patent/GB2088398A/en not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4535174A (en) * | 1984-11-02 | 1985-08-13 | General Electric Company | Free-radical initiators and method for making |
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