Thioalkenylphosphonic acid ester and process for the preparation thereof
AssigneeAgency of Industrial Science and Technology
InventorsLi-Biao Han, Masato Tanaka
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Abstract
A phosphonic acid ester compound of the formula: R1C(SR3)═CHP(═O)(OR2)2 or [P(═O)(OR2)2]CH═C(SR3)—R4—C(SR3)═CH[P(═O)(OR2)2] wherein R1 represents a monovalent group selected from hydrogen, alkyl, cycloalkyl, cycloalkenyl, aryl, aralkyl, alkenyl and silyl, R2 and R3 each represent aryl and R4 represents alkylene or cycloalkylene. The ester compound is produced by reaction of an acetylene compound, R1C≡CH or HC≡C—R4—C≡CH, with with a phosphorothioate, (R2O)2P(═O)SR3, in the presence of a palladium complex catalyst.
Claims4
A process for the preparation of a thioalkenylphosphonic acid ester of the following formula (I):
- R1C(SR3)═CHP(═O)(OR2)2 (I)
- wherein R1 stands for a monovalent group selected from hydrogen atom, an alkyl group, a cycloalkyl group, a cycloalkenyl group, an aryl group, an aralkyl group, an alkenyl group and a silyl group, R2 stands for an aryl group and R3 stands for an aryl group, comprising reacting an acetylene compound of the following formula (II):
- R1C≡CH (II)
- wherein R1 is as defined above, with a phosphorothioate of the following formula (III):
- (R2O)2P(═O)SR3 (III)
- wherein R2 and R3 are as defined above, in the presence of a palladium complex catalyst.
A process for the preparation of a bis(thioalkenyl)phosphonic acid ester of the following formula (IV):
- [P(═O)(OR2)2]CH═C(SR3)—R4—C(SR3)═CH[P(═O)(OR2)2] (IV)
- wherein R2 stands for an aryl group, R3 stands for an aryl group and R4 stands for an alkylene group or a cycloalkylene group, comprising reacting an acetylene compound of the following formula (II):
- HC≡C—R4—C≡CH (V)
- wherein R4 is as defined above, with a phosphorothioate of the following formula (III):
- (R2O)2P(═O)SR3 (III)
- wherein R2 and R3 are as defined above, in the presence of a palladium complex catalyst.
A thioalkenylphosphonic acid ester of the following formula (I):
- R1C(SR )═CHP(═O)(OR2)2 (I)
- wherein R1 stands for a monovalent group selected from hydrogen atom, an alkyl group, a cycloalkyl group, a cycloalkenyl group, an aryl group, an aralkyl group, an alkenyl group and a silyl group and R2 stands for an aryl group and R3 stands for an aryl group.
A bis(thioalkenyl)phosphonic acid ester of the following formula (IV):
- [P(═O)(OR2)2]CH═C(SR3)—R4—C(SR3)═CH[P(═O)(OR2)2] (IV)
- wherein R2 stands for an aryl group, R3 stands for an aryl group and R4 stands for an alkylene group or a cycloalkylene group.
Dependencies are inferred from the claim text.