JP7722322B2 - Method for producing oxadisilacyclopentane compounds - Google Patents

Description

The present invention relates to a method for producing an oxadisilacyclopentane compound.

Oxadisilacyclopentane compounds are useful as raw materials for heat-resistant materials, electronic materials, optical materials, cosmetics, etc.

Proposed methods for producing oxadisilacyclopentane compounds include, for example, reacting 1,2-bis(chlorodimethylsilyl)ethane, obtained by the hydrosilylation reaction of chlorodimethylvinylsilane and chlorodimethylsilane, with water and thermally decomposing the resulting polymer compound (see Patent Document 1), reacting 1,3-bis(chloromethyl)-1,1,3,3-tetramethyldisiloxane with magnesium (see Non-Patent Document 1), and reacting 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, with carbon dioxide to obtain oxadisilacyclopentane as a by-product in the synthesis of a polynuclear tin complex (see Non-Patent Document 2).

Japanese Patent Application Publication No. 5-25182

Pet. Chem. 56,798, 2016 Inorg. Chem. 49, 11133, 2010

In the method of Patent Document 1, 2,2,5,5-tetramethyl-1-oxa-2,5-disilacyclopentane is thought to be produced by the reaction of 1,2-bis(chlorodimethylsilyl)ethane with water. However, the water used and the hydrogen chloride produced by this reaction act as catalysts to promote a ring-opening reaction of the product, which quickly produces a polymeric compound, and the target 2,2,5,5-tetramethyl-1-oxa-2,5-disilacyclopentane is hardly obtained by this reaction. To obtain 2,2,5,5-tetramethyl-1-oxa-2,5-disilacyclopentane from this polymeric compound, a second-stage reaction, a thermal decomposition reaction, is required, which increases the number of steps and is therefore not industrially advantageous.
Furthermore, to obtain the target oxadisilacyclopentane compound by the above-mentioned thermal decomposition, the thermal decomposition reaction must be carried out at a temperature of at least 200°C or higher, and to obtain the target compound at a practical reaction rate, a temperature of 300°C or higher is required. This requires a large amount of energy for production, which is not industrially advantageous.

Furthermore, in the method of Non-Patent Document 1, the reaction must be carried out while adding magnesium as needed 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.

The present invention was developed in consideration of the above circumstances, and aims to provide a method for efficiently and efficiently producing oxadisilacyclopentane compounds.

As a result of extensive research to achieve the above-mentioned objective, the inventors discovered that an oxadisilacyclopentane compound can be obtained without the need for complicated procedures by reacting an azadisilacyclopentane compound with a carboxylic acid compound. Furthermore, because this method does not use water, the ring-opening reaction of the oxadisilacyclopentane compound in the reaction system to form a polymer compound is suppressed, and the oxadisilacyclopentane compound can be obtained in good yield without the need for a high-temperature reaction. This discovery led to the completion of the present invention.

That is, the present invention provides:
1. The following general formula (1):
[In the formula, R ¹ to R ⁴ each independently represent an unsubstituted monovalent hydrocarbon group having 1 to 4 carbon atoms, and 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):
(wherein R ¹ to R ⁴ have the same meaning as defined above, m represents an integer of 0 to 5, n each independently represents an integer of 1 to 5, and the dashed lines represent bonds.)
and an azadisilacyclopentane compound represented by the following general formula (3):
(wherein ^R6 represents a hydrogen atom or an a-valent hydrocarbon group having 1 to 10 carbon atoms which may contain a heteroatom, and a represents an integer of 1 to 5.)
and a carboxylic acid compound represented by the following general formula (4):
(wherein R ¹ to R ⁴ have the same meanings as above.)
A method for producing an oxadisilacyclopentane compound represented by the formula:
2. The method for producing the oxadisilacyclopentane compound of 1 is provided, in which the reaction temperature is 0 to 100°C.

According to the present invention, oxadisilacyclopentane compounds can be produced efficiently and in high yield without producing polymeric compounds or requiring complicated procedures.

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 a carboxylic acid compound.

In general formula (1), R ¹ to R ⁴ each independently represent an unsubstituted monovalent hydrocarbon group having 1 to 4 carbon atoms.
Here, the monovalent hydrocarbon groups of R ¹ to R ⁴ may be linear, branched or cyclic, and examples thereof 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 methyl and ethyl groups are more preferred.

In 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).

(In the formula, R ¹ to R ⁴ have the same meanings as above, and the dashed lines represent bonds.)

Here, the monovalent hydrocarbon group for ^R5 may be linear, branched, or cyclic, and examples thereof include an alkyl group having 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, and more preferably 1 to 6 carbon atoms; an alkenyl group having 2 to 20 carbon atoms, preferably 2 to 10 carbon atoms, and more preferably 2 to 6 carbon atoms; an aryl group having 6 to 20 carbon atoms, preferably 6 to 10 carbon atoms; and an aralkyl group having 7 to 20 carbon atoms, 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 such substituents include alkoxy groups such as methoxy, ethoxy, and (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, from the viewpoints of availability of raw materials and usefulness of the product, preferred monovalent hydrocarbon groups for ^R5 are alkyl groups having 1 to 3 carbon atoms, such as methyl, ethyl, n-propyl, and isopropyl; alkenyl groups having 3 to 5 carbon atoms, such as allyl, 1-butenyl, and 1-pentenyl; and aryl groups having 6 to 8 carbon atoms, such as phenyl.

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

Specific examples of the group represented by general 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 (2,2,5,5-tetramethyl-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, (2,2,5,5-tetrabutyl-1-aza-2,5-disilacyclopent-1-yl)propylaminopropyl group, etc.

Among these, as the group represented by general formula (2) of ^R5 , 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 from the viewpoints of easy availability of raw materials and usefulness of the product.

In general formula (1), ^R5 is more preferably 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.

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 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 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-di-tert-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, etc.

Among these, from the viewpoints of availability of raw materials and usefulness of the product, 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 produced, they may be obtained according to a known method, for example, by a method of subjecting a primary amine compound and a 1,2-bis(chlorosilyl)ethane compound to a dehydrochlorination reaction. When produced, the reaction product may be used as is, or may be purified by distillation or the like.

The carboxylic acid compound used in the present invention is a compound represented by the following general formula (3) (hereinafter referred to as "compound (3)").

In the above general formula (3), R ⁶ is a hydrogen atom or an a-valent hydrocarbon group having 1 to 10 carbon atoms, preferably 1 to 5 carbon atoms, more preferably 1 to 3 carbon atoms, which may contain a heteroatom.
Specific examples thereof include linear alkyl groups such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, and n-decyl 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, and 1-propenyl groups; aryl groups such as phenyl and tolyl groups; and benzyl groups. heteroatom-containing aryl groups such as pyridyl and pyrazyl groups; alkylene groups such as methylene, ethylene, dimethylene, methylethylene, trimethylene, methylpropylene, tetramethylene, hexamethylene, octamethylene, decamethylene and isobutylene groups; arylene groups such as phenylene groups; aralkylene groups such as methylenephenylene and methylenephenylenemethylene groups; and heteroatom-containing alkylene groups such as 1-oxamethylene and 1-azamethylene groups.
Among these, from the viewpoint of easy availability of raw materials, alkyl groups having 1 to 3 carbon atoms are preferred, and methyl and ethyl groups are more preferred.

In the above general formula (3), a is an integer from 1 to 5, preferably an integer of 1 or 2, and more preferably 1.

Specific examples of compound (3) include formic acid, acetic acid, propionic acid, butyric acid, isobutyric acid, hexanoic acid, octanoic acid, 2-ethylhexanoic acid, lauric acid, stearic acid, benzoic acid, acrylic acid, methacrylic acid, oleic acid, linoleic acid, malonic acid, succinic acid, maleic acid, fumaric acid, citraconic acid, phthalic acid, terephthalic acid, and trimellitic acid.

Specific examples of the oxadisilacyclopentane compound represented by general formula (4) (hereinafter referred to as "compound (4)") obtained by the above reaction include 2,2,5,5-tetramethyl-1-oxa-2,5-disilacyclopentane, 2,2,5,5-tetraethyl-1-oxa-2,5-disilacyclopentane, 2,2,5,5-tetrapropyl-1-oxa-2,5-disilacyclopentane, 2,2,5,5-tetraisopropyl-1-oxa-2,5-disilacyclopentane, 2,2,5,5-tetrabutyl-1-oxa-2,5-disilacyclopentane, 2,5-diethyl-2,5-dimethyl-1-oxa-2,5-disilacyclopentane, and 2,5-di-tert-butyl-2,5-dimethyl-1-oxa-2,5-disilacyclopentane.

The compounding ratio of the above compound (1) and compound (3) is not particularly limited, but from the standpoint of reactivity and productivity, 0.6 to 20.0 moles of compound (3) per mole of azadisilacyclopentane moiety in compound (1) is preferred, and 0.8 to 10.0 moles is more preferred.

The above reaction can be carried out without a solvent.
In this case, compound (1) may be added to compound (3), or compound (3) may be added to compound (1).

The reaction can also be carried out in a solvent.
Specific examples of the solvent include any solvent that does not inhibit the reaction, such as hydrocarbon solvents such as pentane, hexane, octane, decane, dodecane, tetradecane, cyclohexane, heptane, isooctane, benzene, toluene, xylene, mesitylene, and tetralin; 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.

When a solvent is used, the order of compound (1), compound (3), and solvent may be determined as desired, but it is preferable to mix a mixture of compound (1) and solvent with compound (3), and it is more preferable to add compound (3) to a mixture of compound (1) and solvent.

The reaction temperature for the above reaction is not particularly limited, but is preferably 0 to 100°C, more preferably 15 to 85°C, even more 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, even more preferably 1 to 7 hours, and even more preferably 1 to 5 hours.
The reaction may be carried out in air or in an inert gas atmosphere such as nitrogen or argon.

In the present invention, the reaction in which compound (1) is converted into the target compound (4) is presumed to proceed as shown in the following reaction formula:

First, compound (1) reacts with compound (3) to produce intermediate compound (5), which is then converted into compound (4) and amide compound (6) in a subsequent ring-closure reaction. Because this reaction does not use water and does not produce water, a polymerization reaction due to the ring-opening reaction of the oxadisilacyclopentane compound with water does not proceed. Therefore, the oxadisilacyclopentane compound can be obtained in high yield.

The reaction liquid thus obtained can be filtered and separated as necessary, and the desired product can be obtained using conventional methods such as distillation and removal of low-boiling compounds.

The present invention will be explained in more detail below using examples and comparative examples, but the present invention is not limited to the following examples.

[Example 1]
A flask equipped with a stirrer, reflux condenser, dropping funnel, and thermometer was charged with 159.4 g (1.0 mol) of 2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane, and 126.2 g (2.1 mol) of acetic acid was added dropwise over 30 minutes at 45-55°C, followed by stirring at that temperature for 2 hours. The resulting solid was removed by filtration, and the filtrate was distilled. 132.3 g of 2,2,5,5-tetramethyl-1-oxa-2,5-disilacyclopentane was obtained as a fraction with a boiling point of 49-50°C/6.0 kPa (yield: 83%).

[Example 2]
A flask equipped with a stirrer, reflux condenser, dropping funnel, and thermometer was charged with 172.4 g (0.5 mol) of 1,1'-(1,2-ethanediyl)bis(2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane), and 155.6 g (2.1 mol) of propionic acid was added dropwise over 30 minutes at 45-55°C, followed by stirring at that temperature for 2 hours. The two separated layers were separated, and the lower layer was removed, followed by distillation of the upper layer. 136.3 g of 2,2,5,5-tetramethyl-1-oxa-2,5-disilacyclopentane was obtained as a fraction with a boiling point of 49-50°C/6.0 kPa (yield: 85%).

[Example 3]
A flask equipped with a stirrer, reflux condenser, dropping funnel, and thermometer was charged with 515.9 g (5.0 mol) of diethylenetriamine, and 215.3 g (1.0 mol) of 1,2-bis(chlorodimethylsilyl)ethane was added dropwise over 1 hour at 100-110°C, followed by stirring at that temperature for 1 hour. The lower layer, which separated into two layers, was removed, yielding a reaction solution of bis[(2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopent-1-yl)ethyl]amine. Subsequently, 155.6 g (2.1 mol) of propionic acid was added dropwise over 30 minutes at 45-55°C, followed by stirring at that temperature for 2 hours. The lower layer, which separated into two layers, was removed, and the upper layer was distilled. 114.0 g of 2,2,5,5-tetramethyl-1-oxa-2,5-disilacyclopentane was obtained as a fraction having a boiling point of 49-50° C./6.0 kPa (yield: 71%).

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

Claims (2)

The following general formula (1)
[In the formula, R ¹ to R ⁴ each independently represent an unsubstituted monovalent hydrocarbon group having 1 to 4 carbon atoms, and 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):
(wherein R ¹ to R ⁴ have the same meaning as defined above, m represents an integer of 0 to 5, n each independently represents an integer of 1 to 5, and the dashed lines represent bonds.)
and an azadisilacyclopentane compound represented by the following general formula (3):
(wherein ^R6 represents a hydrogen atom or an a-valent hydrocarbon group having 1 to 10 carbon atoms which may contain a heteroatom, and a represents an integer of 1 to 5.)
and a carboxylic acid compound represented by the following general formula (4):
(wherein R ¹ to R ⁴ have the same meanings as above.)
A method for producing an oxadisilacyclopentane compound represented by the formula: The method for producing an oxadisilacyclopentane compound according to claim 1, wherein the reaction temperature is 0 to 100°C.