Method for producing oxadisilacyclopentane compound

Abstract

To provide a method allowing efficient and high-yield production of an oxadisilacyclopentane compound.SOLUTION: A production method of an oxadisilacyclopentane compound represented by the general formula (3) in the figure comprises reacting water with an azadisilacyclopentane compound represented by the general formula (1) in the figure. In the general formula (1), R1 to R4 each independently represent a C1-4 unsubstituted monovalent hydrocarbon group. In the general formula (3), R1 to R4 are the same as those in the general formula (1).SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a method for producing an oxadisilacyclopentane compound. [Background technology]

[0002] Oxadisilacyclopentane compounds are useful as raw materials for heat-resistant materials, electronic materials, optical materials, cosmetics, and the like.

[0003] Examples of methods proposed for producing an oxadisilacyclopentane compound include a method in which 1,2-bis(chlorodimethylsilyl)ethane, obtained by the hydrosilylation reaction of chlorodimethylvinylsilane and chlorodimethylsilane, is reacted with water and the resulting polymer compound is thermally decomposed (see Patent Document 1), a method in which 1,3-bis(chloromethyl)-1,1,3,3-tetramethyldisiloxane is reacted with magnesium (see Non-Patent Document 1), and a method in which bis(2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentyl)tin, synthesized from 2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane and tin(II) chloride, is reacted with carbon dioxide to obtain the compound as a by-product in the synthesis of a polynuclear tin complex (see Non-Patent Document 2). [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Japanese Patent Application Publication No. 5-25182 [Non-patent literature]

[0005] [Non-Patent Document 1] Pet.Chem.56,798(2016) [Non-Patent Document 2] Inorg. Chem. 49, 11133 (2010) Summary of the Invention [Problem to be solved by the invention]

[0006] In the method of Patent Document 1, 2,2,5,5-tetramethyl-1-oxa-2,5-disilacyclopentane is produced by the reaction of 1,2-bis(chlorodimethylsilyl)ethane with water, and the hydrogen chloride produced by this reaction acts as a catalyst to promote a ring-opening reaction, which quickly produces a polymer compound. Therefore, in order to obtain 2,2,5,5-tetramethyl-1-oxa-2,5-disilacyclopentane from this polymer compound, a thermal decomposition reaction is required. However, to obtain the target oxadisilacyclopentane compound by thermal decomposition, a temperature of at least 200°C is required, and to obtain the target compound at a practical reaction rate, a temperature of 300°C or higher is required. Since a large amount of energy is required for the production, this is not industrially advantageous.

[0007] Furthermore, in the method of Non-Patent Document 1, the reaction must be carried out while adding magnesium from time to time in order to suppress side reactions, which makes the operation complicated and not industrially advantageous. Furthermore, the method of Non-Patent Document 2 not only requires two-step reactions to obtain the target oxadisilacyclopentane compound, but also has a low yield and requires the use of a highly toxic tin compound, making it industrially unadvantageous.

[0008] The present invention has been made in view of the above circumstances, and an object of the present invention is to provide a method for producing an oxadisilacyclopentane compound efficiently and in high yield. [Means for solving the problem]

[0009] As a result of intensive research conducted by the present inventors in order to achieve the above-mentioned object, it has been found that an oxadisilacyclopentane compound can be obtained by reacting an azadisilacyclopentane compound with water, without the need for a high-temperature reaction or complicated operations, and further, that in the method for obtaining an oxadisilacyclopentane compound in this manner, the ring-opening reaction of the oxadisilacyclopentane compound in the reaction system to produce a polymer compound can be suppressed, thereby completing the present invention.

[0010] That is, the present invention provides 1. The following general formula (1) [ka] [In the formula, R 1 ~R 4 each independently represents an unsubstituted monovalent hydrocarbon group having 1 to 4 carbon atoms; R 5 represents a hydrogen atom, a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, or a group represented by the following general formula (2): [ka] (In the formula, R 1 ~R 4 has the same meaning as above, m is an integer of 0 to 5, and n is an integer of 1 to 5. The dashed line represents a bond. represents a group represented by the following formula: and reacting an azadisilacyclopentane compound represented by the following general formula (3): [ka] (In the formula, R 1 ~R 4 has the same meaning as above.) A method for producing an oxadisilacyclopentane compound represented by the formula: 2. A method for producing an oxadisilacyclopentane compound according to 1, in which an acid compound is used as a catalyst. 3. The method for producing an oxadisilacyclopentane compound according to 2, wherein the acid compound is a carboxylic acid. 4. The method for producing an oxadisilacyclopentane compound according to any one of 1 to 3, wherein the reaction temperature is 0 to 100° C. to provide. Effect of the Invention

[0011] According to the present invention, an oxadisilacyclopentane compound useful as a raw material compound for heat-resistant materials, electronic materials, optical materials, cosmetics, etc. can be efficiently and efficiently produced in high yield. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0012] The present invention will be specifically described below. The method for producing an oxadisilacyclopentane compound of the present invention involves reacting an azadisilacyclopentane compound represented by the following general formula (1) (hereinafter referred to as "compound (1)") with water to obtain an oxadisilacyclopentane compound represented by the following general formula (3) (hereinafter referred to as "compound (3)").

[0013] [ka]

[0014] In the general formulas (1) and (3), R 1 ~R 4 each independently represents an unsubstituted monovalent hydrocarbon group having 1 to 4 carbon atoms. Here, R 1 ~R 4 The unsubstituted monovalent hydrocarbon group having 1 to 4 carbon atoms may be linear, branched or cyclic, and examples of the group include alkyl and alkenyl groups. Specific examples thereof include linear alkyl groups such as methyl, ethyl, n-propyl, and n-butyl groups; branched alkyl groups such as isopropyl, isobutyl, sec-butyl, and tert-butyl groups; cyclic alkyl groups such as cyclopropyl and cyclobutyl groups; and alkenyl groups such as vinyl, allyl, 1-propenyl, isopropenyl, and 1-butenyl groups. Among these, alkyl groups having 1 to 3 carbon atoms are preferred, and a methyl group and an ethyl group are more preferred.

[0015] In the general formula (1), R 5 represents a hydrogen atom, a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, or a group represented by the following general formula (2).

[0016] [ka] (In the formula, R1 ~R 4 has the same meaning as above, and the dashed line represents a bond.

[0017] Here, R 5 The substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms may be linear, branched, or cyclic, and examples thereof include an alkyl group having 1 to 20, preferably 1 to 10, and more preferably 1 to 6 carbon atoms; an alkenyl group having 2 to 20, preferably 2 to 10, and more preferably 2 to 6 carbon atoms; an aryl group having 6 to 20, preferably 6 to 10 carbon atoms; and an aralkyl group having 7 to 20, preferably 7 to 10 carbon atoms. Specific examples thereof include linear alkyl groups such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-decyl, n-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, and n-icosyl groups; branched alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-butyl, thexyl, and 2-ethylhexyl groups; cyclic alkyl groups such as cyclopentyl and cyclohexyl groups; alkenyl groups such as vinyl, allyl, 1-butenyl, and 1-pentenyl groups; aryl groups such as phenyl and tolyl groups; and aralkyl groups such as benzyl groups. In addition, some or all of the hydrogen atoms of these monovalent hydrocarbon groups may be substituted, and specific examples of the substituents include alkoxy groups such as methoxy, ethoxy, (n- or iso)propoxy groups; halogen atoms such as fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms; cyano groups; amino groups; and acyl groups having 2 to 10 carbon atoms. Among these, R 5 From the viewpoints of availability of raw materials and usefulness of the product, preferred monovalent hydrocarbon groups are alkyl groups having 1 to 3 carbon atoms, such as methyl, ethyl, and (n- or iso)propyl groups; alkenyl groups having 3 to 5 carbon atoms, such as allyl, 1-butenyl, and 1-pentenyl groups; and aryl groups, such as phenyl groups.

[0018] In formula (2), m is an integer of 0 to 5, preferably an integer of 0 to 2, and more preferably 0 or 1. n is an integer of 1 to 5, preferably an integer of 1 to 4, and more preferably 2 or 3. A preferred combination of m and n is when m is 0 or 1, and n is 2 or 3.

[0019] Specific examples of the group represented by formula (2) include (2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopent-1-yl)ethyl, (2,2,5,5-tetraethyl-1-aza-2,5-disilacyclopent-1-yl)ethyl, (2,2,5,5-tetrapropyl-1-aza-2,5-disilacyclopent-1-yl)ethyl, (2,2,5,5-tetraisopropyl-1-aza-2,5-disilacyclopent-1-yl)ethyl, (2,2,5,5-tetrabutyl-1-aza-2,5-disilacyclopent-1-yl)ethyl, (2,2, 5,5-tetramethyl-1-aza-2,5-disilacyclopent-1-yl)propyl, (2,2,5,5-tetraethyl-1-aza-2,5-disilacyclopent-1-yl)propyl, (2,2,5,5-tetrapropyl-1-aza-2,5-disilacyclopent-1-yl)propyl, (2,2,5,5-tetraisopropyl-1-aza-2,5-disilacyclopent-1-yl)propyl, (2,2,5,5-tetrabutyl-1-aza-2,5-disilacyclopent-1-yl)propyl, (2,2,5,5-tetramethyl-1-aza-2,5-di silacyclopent-1-yl)ethylaminoethyl, (2,2,5,5-tetraethyl-1-aza-2,5-disilacyclopent-1-yl)ethylaminoethyl, (2,2,5,5-tetrapropyl-1-aza-2,5-disilacyclopent-1-yl)ethylaminoethyl, (2,2,5,5-tetraisopropyl-1-aza-2,5-disilacyclopent-1-yl)ethylaminoethyl, (2,2,5,5-tetrabutyl-1-aza-2,5-disilacyclopent-1-yl)ethylaminoethyl, (2,2,5,5-tetramethyl-1-aza-2 ,5-disilacyclopent-1-yl)propylaminopropyl, (2,2,5,5-tetraethyl-1-aza-2,5-disilacyclopent-1-yl)propylaminopropyl, (2,2,5,5-tetrapropyl-1-aza-2,5-disilacyclopent-1-yl)propylaminopropyl, (2,2,5,5-tetraisopropyl-1-aza-2,5-disilacyclopent-1-yl)propylaminopropyl, and (2,2,5,5-tetrabutyl-1-aza-2,5-disilacyclopent-1-yl)propylaminopropyl groups. Among these, R 5 As the group represented by general formula (2), from the viewpoints of availability of raw materials and usefulness of the product, a (2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopent-1-yl)ethyl group and a (2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopent-1-yl)ethylaminoethyl group are preferred.

[0020] In the general formula (1), R 5 As the alkyl group, a hydrogen atom, an allyl group, a 2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopent-1-yl)ethyl group, or a (2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopent-1-yl)ethylaminoethyl group is more preferable.

[0021] Specific examples of compound (1) include 2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane, 2,2,5,5-tetraethyl-1-aza-2,5-disilacyclopentane, 2,2,5,5-tetrapropyl-1-aza-2,5-disilacyclopentane, 2,2,5,5-tetraisopropyl-1-aza-2,5-disilacyclopentane, 2,2,5,5-tetrabutyl-1-aza-2,5-disilacyclopentane, 2,5-diethyl-2,5-dimethyl-1-aza-2,5-disilacyclopentane, 2,5-ditert-butyl-2,5- Dimethyl-1-aza-2,5-disilacyclopentane, 1,2,2,5,5-pentamethyl-1-aza-2,5-disilacyclopentane, 1-methyl-2,2,5,5-tetraethyl-1-aza-2,5-disilacyclopentane, 1-methyl-2,2,5,5-tetrapropyl-1-aza-2,5-disilacyclopentane, 1-methyl-2,2,5,5-tetraisopropyl-1-aza-2,5-disilacyclopentane, 1-methyl-2,2,5,5-tetrabutyl-1-aza-2,5-disilacyclopentane, 2,5-diethyl-1,2,5-trimethyl -1-aza-2,5-disilacyclopentane, 2,5-ditert-butyl-1,2,5-dimethyl-1-aza-2,5-disilacyclopentane, 1-ethyl-2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane, 1,2,2,5,5-pentaethyl-1-aza-2,5-disilacyclopentane, 1-ethyl-2,2,5,5-tetrapropyl-1-aza-2,5-disilacyclopentane, 1-ethyl-2,2,5,5-tetraisopropyl-1-aza-2,5-disilacyclopentane, 1-ethyl-2,2,5,5-tetrabutyl -1-aza-2,5-disilacyclopentane, 1-ethyl-2,5-diethyl-2,5-dimethyl-1-aza-2,5-disilacyclopentane, 1-ethyl-2,5-ditert-butyl-2,5-dimethyl-1-aza-2,5-disilacyclopentane, 1-allyl-2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane, 1-allyl-2,2,5,5-tetraethyl-1-aza-2,5-disilacyclopentane, 1-allyl-2,2,5,5-tetrapropyl-1-aza-2,5-disilacyclopentane, 1-allyl-2,2,5,5-tetraisopropyl-1-aza-2,5-disilacyclopentane, 1-allyl-2,2,5,5-tetrabutyl-1-aza-2,5-disilacyclopentane, 1-allyl-2,5-diethyl-2,5-dimethyl-1-aza-2,5-disilacyclopentane, 1-allyl-2,5-ditert-butyl-2,5-dimethyl-1-aza-2,5-disilacyclopentane, 1-phenyl-2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane, 1-phenyl-2,2,5,5-tetraethyl-1-aza-2,5-disilacyclopentane, 1-phenyl-2,2,5,5-tetrapropyl-1-aza-2,5-disilacyclopentane, 1 -phenyl-2,2,5,5-tetraisopropyl-1-aza-2,5-disilacyclopentane, 1-phenyl-2,2,5,5-tetrabutyl-1-aza-2,5-disilacyclopentane, 1-phenyl-2,5-diethyl-2,5-dimethyl-1-aza-2,5-disilacyclopentane, 1-phenyl-2,5-ditert-butyl-2,5-dimethyl-1-aza-2,5-disilacyclopentane, 1,1'-(1,2-ethanediyl)bis(2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane), bis[(2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopent-1-yl)ethyl]amine, and the like. Among these, from the viewpoint of availability of raw materials and usefulness of products, 2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane, 1-allyl-2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane, 1,1'-(1,2-ethanediyl)bis(2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane), and bis[(2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopent-1-yl)ethyl]amine are preferred. These compounds may be commercially available or may be produced. When producing them, they may be produced according to a conventionally known method, for example, by reacting a primary amine compound with a 1,2-bis(chlorosilyl)ethane compound.

[0022] The mixing ratio of the compound (1) to water is not particularly limited, but from the standpoint of reactivity and productivity, the ratio of water to 1 mole of the azadisilacyclopentane moiety of compound (1) is preferably 0.5 to 50.0 moles, and more preferably 0.8 to 20.0 moles.

[0023] The above reaction proceeds without a catalyst, but a catalyst can be used to increase the reaction rate. The catalyst used is preferably an acid compound, and specific examples thereof include inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid, etc.; sulfonic acid compounds such as methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, dodecylbenzenesulfonic acid, trifluoromethanesulfonic acid, etc.; carboxylic acids such as acetic acid, propionic acid, butyric acid, malonic acid, succinic acid, maleic acid, benzoic acid, phthalic acid, etc.; salts of the above-mentioned acids; and Lewis acid compounds such as aluminum chloride, zinc chloride, titanium tetrachloride, etc. Among these, carboxylic acids are particularly preferred, and acetic acid is more preferred.

[0024] When a catalyst is used, the amount of the catalyst used is not particularly limited, but from the viewpoints of reactivity and productivity, the amount is preferably 0.0001 to 0.5 mol, and more preferably 0.001 to 0.2 mol, per 1 mol of compound (1).

[0025] The above reaction can be carried out without a solvent. In this case, compound (1) may be added to water or water may be added to compound (1), but from the viewpoint of improving the reaction rate, a method of adding compound (1) to water is preferred, and a method of dropping compound (1) into water is more preferred. When an acid compound is used as a catalyst, it is preferable to use it by mixing it with water.

[0026] The above reaction can also be carried out using a solvent. Specific examples of the solvent include any solvent that does not inhibit the reaction, such as hydrocarbon solvents such as pentane, hexane, cyclohexane, heptane, isooctane, benzene, toluene, and xylene; ether solvents such as diethyl ether, tetrahydrofuran, dioxane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, dipropylene glycol dimethyl ether, and dipropylene glycol diethyl ether; ester solvents such as ethyl acetate, butyl acetate, and propylene glycol monomethyl ether acetate; aprotic polar solvents such as acetonitrile, N,N-dimethylformamide, N-methylpyrrolidone, and dimethyl sulfoxide; chlorinated hydrocarbon solvents such as dichloromethane and chloroform; and alcohol solvents such as methanol and ethanol. These may be used alone or in combination of two or more. Among these, ether solvents, ester solvents, and aprotic polar solvents are preferred from the viewpoint of improving the reaction rate due to improved compatibility with water.

[0027] When a solvent is used, the order of compound (1), water, and the solvent may be arbitrary, but it is preferable to mix the mixture of compound (1) and the solvent with water, more preferable to add water to the mixture of compound (1) and the solvent, and even more preferable to drop water into the mixture. In this case, water may be used as a mixture with the solvent. The mixing ratio of water and the solvent is not particularly limited, but the ratio of water / solvent is preferably 1 / 0.5 to 1 / 5 by mass. When a catalyst is used, it may be added to the mixture of compound (1) and the solvent, or to the water.

[0028] The reaction temperature of the above reaction is not particularly limited, but is preferably 0 to 100°C, more preferably 15 to 85°C, further preferably 20 to 80°C, and even more preferably 20 to 70°C. The reaction time is not particularly limited, but is preferably 1 to 15 hours, more preferably 1 to 10 hours, further preferably 1 to 7 hours, and even more preferably 1 to 5 hours. The above reaction may be carried out in air or in an inert gas atmosphere such as nitrogen or argon.

[0029] Compound (1) reacts irreversibly with water under mild conditions and is converted to the desired compound (3). In addition, in the method for obtaining compound (3) in this manner, the ring-opening reaction of compound (1) in the reaction system to produce a polymer compound is suppressed. Therefore, this method is more advantageous than the conventional method of thermally decomposing a polymer compound produced by reacting 1,2-bis(chlorodimethylsilyl)ethane with water, which requires a high-temperature reaction.

[0030] From the reaction mixture thus obtained, separation can be carried out as necessary, and the target product can be obtained by a conventional method such as distillation or removal of low boiling point compounds. EXAMPLES

[0031] The present invention will be described in more detail below with reference to examples and comparative examples, but the present invention is not limited to the following examples.

[0032] [Example 1] A flask equipped with a stirrer, reflux condenser, dropping funnel and thermometer was charged with 200g (11.1 mol) of water and 2.0g (0.03 mol) of acetic acid, and 159.4g (1.0 mol) of 2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane was added dropwise over 30 minutes at 25-35°C, and the mixture was stirred for 3 hours at that temperature. After the reaction, the lower layer, which separated into two layers, was removed, and the upper layer was distilled. 105.8g of 2,2,5,5-tetramethyl-1-oxa-2,5-disilacyclopentane was obtained as a fraction with a boiling point of 49-50°C / 6.0kPa (yield 66%).

[0033] [Example 2] In a flask equipped with a stirrer, reflux condenser, dropping funnel and thermometer, 159.4g (1.0 mol) of 2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane and 400g of dipropylene glycol dimethyl ether were charged, and 22.5g (1.25 mol) of water was added dropwise over 30 minutes at 45-55°C, and the mixture was stirred for 2 hours at that temperature. The reaction liquid was distilled, and 115.3g of 2,2,5,5-tetramethyl-1-oxa-2,5-disilacyclopentane was obtained as a fraction with a boiling point of 49-50°C / 6.0kPa (yield 72%).

[0034] [Example 3] In a flask equipped with a stirrer, a reflux condenser, a dropping funnel and a thermometer, 159.4g (1.0 mol) of 2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane and 350g of tetrahydrofuran were charged, and 18.9g (1.05 mol) of water was added dropwise over 2 hours at 45-55°C, and the mixture was stirred for 2 hours at that temperature. The reaction liquid was distilled, and 132.0g of 2,2,5,5-tetramethyl-1-oxa-2,5-disilacyclopentane was obtained as a fraction with a boiling point of 49-50°C / 6.0kPa (yield 82%).

[0035] [Example 4] In a flask equipped with a stirrer, a reflux condenser, a dropping funnel and a thermometer, 199.4g (1.0 mol) of 1-allyl-2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane and 400g of tetrahydrofuran were charged, and a mixture of 36.0g (1.5 mol) of water and 36.0g of tetrahydrofuran was added dropwise over 8 hours at 45-55°C, and the mixture was stirred for 2 hours at that temperature. The reaction liquid was distilled, and 110.5g of 2,2,5,5-tetramethyl-1-oxa-2,5-disilacyclopentane was obtained as a fraction with a boiling point of 49-50°C / 6.0kPa (yield 69%).

[0036] [Example 5] In a flask equipped with a stirrer, reflux condenser, dropping funnel and thermometer, 172.4g (0.5 mol) of 1,1'-(1,2-ethanediyl)bis(2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane) and 400g of tetrahydrofuran were charged, and a mixture of 36.0g (1.5 mol) of water and 36.0g of tetrahydrofuran was added dropwise over 8 hours at 65-75°C, and the mixture was stirred for 2 hours at that temperature. The reaction liquid was distilled, and 114.5g of 2,2,5,5-tetramethyl-1-oxa-2,5-disilacyclopentane was obtained as a fraction with a boiling point of 49-50°C / 6.0kPa (yield 71%).

[0037] [Example 6] In a flask equipped with a stirrer, a reflux condenser, a dropping funnel and a thermometer, 194.0g (0.5 mol) of bis[(2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopent-1-yl)ethyl]amine and 400g of tetrahydrofuran were charged, and a mixture of 36.0g (1.5 mol) of water and 36.0g of tetrahydrofuran was dropped at 65-75°C over 8 hours, and the mixture was stirred at that temperature for 2 hours. The reaction liquid was distilled, and 128.8g of 2,2,5,5-tetramethyl-1-oxa-2,5-disilacyclopentane was obtained as a fraction with a boiling point of 49-50°C / 6.0kPa (yield 80%).

[0038] [Comparative Example 1] 215.3g (1.0 mol) of 1,2-bis(chlorodimethylsilyl)ethane was charged into a flask equipped with a stirrer, reflux condenser, dropping funnel and thermometer, and 900g (50.0 mol) of water was dropped at 50-60°C over 1 hour, and the mixture was stirred at that temperature for 1 hour. After the reaction, the lower layer, which separated into two layers, was removed, and 6.4g of 50% by mass potassium hydroxide aqueous solution was added to the upper layer, and the generated polymer compound was subjected to a thermal decomposition reaction. The generation of the target 2,2,5,5-tetramethyl-1-oxa-2,5-disilacyclopentane was confirmed when the internal temperature reached 250°C or higher. After a 5-hour reaction at 370°C, distillation was performed. 78.3g of 2,2,5,5-tetramethyl-1-oxa-2,5-disilacyclopentane was obtained as a fraction with a boiling point of 49-50°C / 6.0kPa (yield 49%).

Claims

1. The following general formula (1) 【Chemistry 1】 [In the formula, R 1 ~R 4 each independently represents an unsubstituted monovalent hydrocarbon group having 1 to 4 carbon atoms; R 5 represents a hydrogen atom, a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, or a group represented by the following general formula (2): 【Chemistry 2】 (In the formula, R 1 ~R 4 has the same meaning as above, m is an integer of 0 to 5, and n is an integer of 1 to 5. The dashed line represents a bond. represents a group represented by the following formula: and reacting an azadisilacyclopentane compound represented by the following general formula (3): 【Chemistry 3】 (In the formula, R 1 ~R 4 represents the same meaning as above.) A method for producing an oxadisilacyclopentane compound represented by the following formula:

2. 2. The method for producing an oxadisilacyclopentane compound according to claim 1, wherein an acid compound is used as the catalyst.

3. 3. The method for producing an oxadisilacyclopentane compound according to claim 2, wherein the acid compound is a carboxylic acid.

4. The method for producing an oxadisilacyclopentane compound according to any one of claims 1 to 3, wherein the reaction temperature is 0 to 100°C.

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