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 [R.sup.1 R.sup.2 R.sup.3 P--CR.sup.4 R.sup.5 R.sup.6 ]X, comprising ball-milling a phosphine of the formula R.sup.1 R.sup.2 R.sup.3 P with a compound of the formula XCR.sup.4 R.sup.5 R.sup.6 ; a method of preparing a phosphorus ylide of the formula R.sup.1 R.sup.2 R.sup.3 P.dbd.CR.sup.4 R.sup.5, comprising ball-milling a phosphonium salt of the formula [R.sup.1 R.sup.2 R.sup.3 P--HCR.sup.4 R.sup.5 ]X in the presence of a base; and a method of preparing an olefin of the formula R.sup.4 R.sup.5 C.dbd.CR.sup.7 H or R.sup.4 R.sup.5 C.dbd.CR.sup.7 R.sup.8, comprising ball-milling a phosphorus ylide of the formula R.sup.1 R.sup.2 R.sup.3 P.dbd.CR.sup.4 R.sup.5 with a compound of the formula R.sup.7 C(O)H or R.sup.7 C(O)R.sup.8. 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)
- Sponsoring Organization:
- USDOE
- DOE Contract Number:
- W-7405-ENG-82
- Assignee:
- Iowa State University Research Foundation, Inc. (Ames, IA)
- Patent Number(s):
- 6,730,812
- Application Number:
- 10/358,552
- OSTI ID:
- 1174833
- Country of Publication:
- United States
- Language:
- English
Mechanically Induced Solid-State Generation of Phosphorus Ylides and the Solvent-Free Wittig Reaction
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journal | June 2002 |
Kumulierte Ylide; XIII 1 : Diethoxyvinylidentriphenylphosphoran als Reagenz zur Herstellung von Carbonsäure-ethylestern in aprotischen Lösungsmitteln
|
journal | January 1981 |
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