Microwave‐Assisted Elimination Reaction of trans‐4‐(4‐Fluorophenyl)‐3‐chloromethyl‐1‐methylpiperidine on Alumina

References

• Engelstoft , M. and Hansen , J. B. 1996 . Synthesis and 5HT modulating activity of stereoisomers of 3‐phenoxymethyl‐4‐phenylpiperidines . Acta Chem. Scand. , 50 : 164 – 169 . [PUBMED] [INFOTRIEVE]
   Google Scholar
• Christensen , J. A. and Squires , F. R. 4‐Phenylpiperidine Compounds . US Patent 4,007,196 . February 8, 1977 .
   Google Scholar
• Dechant , K. L. and Clissold , S. P. 1991 . Paroxetine—a review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potential in depressive illness . Drugs , 41 : 225 – 253 . [PUBMED] [INFOTRIEVE]
   PubMed Web of Science ®Google Scholar
• Navrátilová , H. and Potáček , M. 2001 . Enantiomeric enrichment of (+)‐(3R,4S)‐4‐(4‐fluorophenyl)‐3‐hydroxymethyl‐1‐methylpiperidine by crystallization . Enantiomer , 6 : 333 – 338 . [CSA]
   Google Scholar
• Cromwell , N. H. , Ayer , R. P. and Foster , P. W. 1960 . Elimination reactions of α‐halogenated ketons. I. Dehydrobromination of 2‐benzyl‐2‐bromo‐4,4‐dimethyl‐1‐tetralone . J. Am. Chem. Soc. , 82 : 130 – 132 .
   Google Scholar
• Bartsch , R. A. and Bunnet , J. F. 1969 . Orientation of olefin‐forming elimination in reactions of 2‐substituted hexanes with potassium t‐butoxide‐t‐butyl alcohol and sodium methoxide‐methanol . J. Am. Chem. Soc. , 91 : 1376 – 1382 .
   Web of Science ®Google Scholar
• Veeravagu , P. , Arnold , R. T. and Eigenmann , E. W. 1964 . Competitive elimination‐substitution reactions. Some dramatic differences between bromides and tosylates . J. Am. Chem. Soc. , 86 : 3072 – 3075 .
   Google Scholar
• Beltram , P. , Biale , G. , Lloyd , D. J. , Parker , A. J. , Ruane , M. and Winstein , S. 1972 . The E2C mechanism in elimination reactions. V. Elimination from five‐ and six‐membered alicyclics . J. Am. Chem. Soc. , 94 : 2240 – 2256 .
   Google Scholar
• Muir , D. M. and Parker , A. J. 1976 . The E2C mechanism in elimination reactions. 8. Interaction of conjugating substituents with E2C‐ and E2H‐like transition states . J. Org. Chem. , 41 : 3201 – 3204 .
   Google Scholar
• Akiyama , S. , Nakatsuji , S. , Nomura , K. , Matsuda , K. and Nakashima , K. 1991 . Direct CC tripple bond formation from the CC double bond with potassium tert‐butoxide in dimethylformamide containing trace amounts of oxygen . J. Chem. Soc. Chem. Commun. , : 948 – 950 . [CROSSREF]
   Google Scholar
• Kabalka , G. W. and Pagni , R. M. 1997 . Organic reactions on alumina . Tetrahedron , 53 : 7999 – 8065 . [CROSSREF]
   Web of Science ®Google Scholar
• Závada , J. and Pánková , M. 1990 . Preferential cis‐olefin formation: a striking resemblance between alkali‐alkoxide and alumina promoted eliminations in low polar solvents . Collect. Czech. Chem. Commun. , 55 : 704 – 709 .
   Google Scholar
• Pearson , D. E. and Bühler , C. A. 1974 . Potassium tert‐butoxide in synthesis . Chem. Rev. , 74 : 45 – 86 .
   Google Scholar
• Barry , J. , Bram , G. , Decodts , G. , Loupy , A. , Pigeon , P. and Sansoulet , J. 1984 . Solid‐liquid phase‐transfer catalysis reactions without solvent; very mild conditions for β‐eliminations . J. Org. Chem. , 49 : 1138 – 1140 .
   Web of Science ®Google Scholar
• Vogel , E. and Klärner , F.‐G. 1968 . 1,2‐Naphthalinoxid . Angew. Chem. , 80 : 402 – 404 .
   Google Scholar
• Wolkoff , P. 1982 . Dehydrobromination of secondary and tertiary alkyl and cycloalkyl bromides with 1,8‐diazabicyclo[5.4.0]undecene‐7‐ene—synthetic applications . J. Org. Chem. , 47 : 1944 – 1948 .
   Web of Science ®Google Scholar
• Loupy , A. , Petit , A. , Hamelin , J. , Texier‐Boullet , F. , Jacquault , P. and Mathé , D. 1998 . New solvent‐free organic synthesis using focused microwaves . J. Synth. Org. Chem. , : 1213 – 1234 .
   Google Scholar
• Saoudi , A. , Hamelin , J. and Benhaoua , H. 1998 . Elimination reaction over solid supports under microwave irradiation: synthesis of functionalized alkenes . Tetrahedron Lett. , 39 : 4035 – 4038 . [CROSSREF]
   Google Scholar
• Bougrin , K. , Soufiaoui , M. , Loupy , A. and Jacquault , P. 1995 . Addition dipolaire 1,3 de la diphénylnitrilimine sur quelques dipolarophiles en milieu sec sous microondes . New J. Chem. , 19 : 213 – 219 .
   Web of Science ®Google Scholar
• Beckett , H. , Casy , A. F. and Iorio , M. A. 1966 . Studies of the elimination of 4‐aryl‐3‐methyl‐4‐piperidinols—III. π–π transitions in some 4‐aryl‐3‐(and 5)‐methyl‐1,2,5,6‐tetrahydropyridines . Tetrahedron , 22 : 2745 – 2750 . [CROSSREF]
   Google Scholar
• March , J. 1992 . Advanced Organic Chemistry: Reactions, Mechanism, and Structures , 4th Ed. 582 John Wiley and Sons . and references therein
   Google Scholar
• Frisch , M. J. , Trucks , G. W. , Schlegel , H. B. , Scuseria , G. E. , Robb , M. A. , Cheeseman , J. R. , Zakrzewski , V. G. , Montgomery , J. A. Jr. , Stratmann , R. E. , Burant , J. C. , Dapprich , S. , Millam , J. M. , Daniels , A. D. , Kudin , K. N. , Strain , M. C. , Farkas , O. , Tomasi , J. , Barone , V. , Cossi , M. , Cammi , R. , Mennucci , B. , Pomelli , C. , Adamo , C. , Clifford , S. , Ochterski , J. , Petersson , G. A. , Ayala , P. Y. , Cui , Q. , Morokuma , K. , Malick , D. K. , Rabuck , A. D. , Raghavachari , K. , Foresman , J. B. , Cioslowski , J. , Ortiz , J. V. , Baboul , A. G. , Stefanov , B. B. , Liu , G. , Liashenko , A. , Piskorz , P. , Komaromi , I. , Gomperts , R. , Martin , R. L. , Fox , D. J. , Keith , T. , Al‐Laham , M. A. , Peng , C. Y. , Nanayakkara , A. , Challacombe , M. , Gill , P. M.W. , Johnson , B. , Chen , W. , Wong , M. W. , Andres , J. L. , Gonzalez , C. , Head‐Gordon , M. , Replogle , E. S. and Pople , J. A. 1998 . Gaussian 98, Revision A.9 Pittsburgh, PA : Gaussian, Inc. .
   Google Scholar