Solvent-free mechanochemical preparation of phosphonium salts, phosphorus ylides, and olefins
The present invention provides a method of preparing a phosphonium salt of the formula [R1R2R3P--CR4R5R6]X, comprising ball-milling a phosphine of the formula R1R2R3P with a compound of the formula XCR4R5R6; a method of preparing a phosphorus ylide of the formula R1R2R3P--CR4R5, comprising ball-milling a phosphonium salt of the formula [R1R2R3P --HCR4R5]X in the presence of a base; and a method of preparing an olefin of the formula R4R5C--CR7H or R4R5C--CR7R8, comprising ball-milling a phosphorus ylide of the formula [R1R2R3P--CR4R5 with a compound of the formula R7C(O)H or R7C(O)R8. The inventive method produces phosphonium salts and phosphorus ylides by mechanical processing solid reagents under solvent-free conditions. The advantages of the present invention over conventional solution methods, include: (1) extremely high selectivity; (2) high yields; (3) low processing temperatures; (4) simple and scalable reactions using commercially available equipment; and (5) the complete elimination of solvents from the reaction.
- Research Organization:
- Iowa State Univ., Ames, IA (United States); Ames Laboratory (AMES), Ames, IA (United States)
- Sponsoring Organization:
- USDOE
- DOE Contract Number:
- W-7405-ENG-82
- Assignee:
- Iowa State University Research Foundation, Inc. (Ames, IA)
- Patent Number(s):
- 7,105,714
- Application Number:
- 10/744,932
- OSTI ID:
- 1175910
- Resource Relation:
- Patent File Date: 2003 Dec 22
- Country of Publication:
- United States
- Language:
- English
Mechanically Induced Solid-State Generation of Phosphorus Ylides and the Solvent-Free Wittig Reaction
|
journal | June 2002 |
Kumulierte Ylide; XIII 1 : Diethoxyvinylidentriphenylphosphoran als Reagenz zur Herstellung von Carbonsäure-ethylestern in aprotischen Lösungsmitteln
|
journal | January 1981 |
Similar Records
Addition of azomethine ylides to C[sub 60]. Synthesis, characterization, and functionalization of fullerene pyrrolidines
Mechanism of the photolysis of 2,6-diphenyl-p-benzoquinone in PCl/sub 3/. Formation of phosphonium quinone-ylide