Synthesis of Dialkyl 2-(2-Oxo-2-phenylethyl)-3-(1,1,1-triphenyl-λ5-phosphanylidene)succinates from Triphenylphosphine, Acetylenic Ester and 4,4,4-Trifluoro-1-phenyl-1,3-butanedione in the Presence of Basic Alumina Powder

Protonation of the highly reactive 1:1 intermediates, produced in the reaction between triphenylphosphine and dialkyl acetylenedicarboxylates, by 4,4,4-trifluoro-1-phenyl-1,3-butanedione leads to vinyltriphenylphosphonium salts, which undergo Michael addition reaction with conjugate base to produce corresponding phosphorus ylides. Basic alumina powder was found to catalyze conversion of the phosphorus ylides to dialkyl 2-(2-oxo-2-phenylethyl)-3-(1,1,1-triphenyl-λ 5 -phosphanylidene)succinates in solvent-free conditions under microwave (0.9 KW, 3 min) and thermal (25°C, 120 min) conditions.

[1]  J. Drabowicz,et al.  From Phosphorus Ylides , 2007 .

[2]  A. Ramazani,et al.  Synthesis and X-Ray Single Crystal Structure of Dialkyl 2-[1-(2,2-Dimethylpropionyl)-3,3-dimethyl-2-oxobutyl]-3- (triphenylphosphoranylidene)succinates , 2006 .

[3]  G. Keglevich,et al.  Efficient synthesis of cyclic β-oxophosphoranes by microwave-assisted reaction of cyclic phosphine oxides and dialkyl acetylenedicarboxylates , 2006 .

[4]  A. Ramazani,et al.  Microwave-Induced Stereoselective Conversion of Dialkyl 2-(1,1,3-Trioxo-1,3-dihydro-2 H -1,2-Benzisothiazol-2-yl)-3-(triphenylphosphoranylidene)succinates to Dialkyl 2-(1,1,3-Trioxo-1,3-dihydro-2 H -1,2-benzisothiazol-2-yl)-2-butendioates in the Presence of Silica-Gel Powder in Solvent-Free Conditio , 2006 .

[5]  G. Keglevich,et al.  A quantum chemical study on the reaction of 1-aryl-1,2-dihydrophosphinine oxides with dimethyl acetylenedicarboxylate , 2005 .

[6]  G. Keglevich,et al.  Synthesis and Reactions of β-Oxophosphoranes / Ylides Containing a Cyclic or Acyclic P-Moiety , 2004 .

[7]  G. Keglevich,et al.  Reactions of β-oxo-α,β-bis(alkoxycarbonyl)phosphonium ylides based on P-heterocycles , 2004 .

[8]  V. Nair,et al.  Strategies for heterocyclic construction via novel multicomponent reactions based on isocyanides and nucleophilic carbenes. , 2003, Accounts of chemical research.

[9]  A. Ramazani,et al.  Vinyltriphenylphosphonium Salt Mediated One-Pot Stereoselective Synthesis of Dialkyl ( E )-2-(2-methyl-5-oxo-1-cyclopentenyl)-2-butenedioates , 2003 .

[10]  A. Ramazani,et al.  Vinylphosphonium Salt Mediated One-Pot Stereoselective Synthesis of Dialkyl 3,3-Diacetyl-3 a -hydroxy-8-oxo-2,3,3 a ,8-tetrahydrocyclopenta-[ a ]indene-1,2-dicarboxylates , 2003 .

[11]  A. Ramazani,et al.  Tributylphosphine Catalyzed Stereoselective N -Vinylation of Phthalimide and Succinimide , 2003 .

[12]  A. Ramazani,et al.  Tributylphosphine Catalyzed O -Vinylation of 2-Hydroxy-3-methyl-2-cyclopenten-1-one , 2003 .

[13]  S. Lovas,et al.  Structure and stability of oxaphosphetes formed as intermediates in the reaction of tertiary phosphine oxides and acetylenic derivatives , 2002 .

[14]  A. Ramazani,et al.  Silica Gel Catalyzed Stereoselective Conversion of Dialkyl 2-(3-acetyl-4-hydroxy-1-naphthyl)-3-(triphenylphosphoranylidene) butanedioates to Dialkyl 2-(3-acetyl-4-hydroxy-1-naphthyl)-2-butenedioates in Solvent-Free Conditions , 2002 .

[15]  M. Kidwai,et al.  Solventless synthesis of thiohydantoins over K2CO3 , 2001 .

[16]  N. Deka,et al.  Microwave mediated solvent-free acetylation of deactivated and hindered phenols , 2001 .

[17]  A. Ramazani,et al.  ONE-STEP, THREE-COMPONENT SYNTHESIS OF DIALKYL 2-(IMIDO-N-YL)-3-(TRIPHENYLPHOSPHORANYLIDENE) BUTANEDIOATES , 2001 .

[18]  A. Ramazani,et al.  One-pot, four-component synthesis of dialkyl [indane-1,3-dione-2-ylidene]alkoxysuccinates , 2000 .

[19]  O. Kolodiazhnyi.  Phosphorus ylides : chemistry and application in organic synthesis , 1999 .

[20]  A. Ramazani,et al.  ONE-POT STEREOSELECTIVE SYNTHESIS OF DIMETHY (2-HYDROXY-4,4-DIMETHYLCYCLOHEX-1-EN-6-ONE-1-YL)-3-(DIPHENYLPHOSPHONATO)BUTANEDIOATE , 1997 .

[21]  A. Ramazani,et al.  Triphenylphosphine Catalyzed Stereoselective Synthesis of O-Vinyloximes , 1997 .

[22]  O. Kolodiazhnyi.  Methods of preparation of C-substituted phosphorus ylides and their application in organic synthesis , 1997 .

[23]  A. Ramazani,et al.  Synthesis of Densely Functionalized N-Hydroxypyrroles Mediated by Vinyltriphenylphosphonium Salt , 1996 .

[24]  R. Cherkasov,et al.  Heterophosphacyclanes in organic synthesis , 1994 .

[25]  M. Zabłocka,et al.  Preparation of Scalemic P-Chiral Phosphines and Their Derivatives , 1994 .

[26]  A. Reitz,et al.  The Wittig olefination reaction and modifications involving phosphoryl-stabilized carbanions. Stereochemistry, mechanism, and selected synthetic aspects , 1989 .

[27]  W. C. Kaska.  The coordination chemistry of ylides , 1983 .

[28]  K. B. Becker.  Cycloalkenes by intramolecular wittig reaction , 1980 .

[29]  J. Cadogan.  Organophosphorus reagents in organic synthesis , 1979 .

[30]  H. Bestmann.  Phosphacumulenylide und Phosphaallenylide , 1977 .