Selective Sulfenylative Desulfonylation or Decarbalkoxylation of α-Sulfonyl Malonates with DABCO or Bu₃N: Reactivity and Conformational Analysis

REFERENCES

• Smith , M. B. Organic Synthesis, , 2nd ed. ; McGraw-Hill : New York , 2002 ; Carey , F. A. ; Sundberg , R. J. Advanced Organic Chemistry, , 4th ed. ; Plenum Press : New York , 2000 .
   Google Scholar
• Kürti , L. ; Czakó , B. Strategic Applications of Named Reactions in Organic Synthesis ; Elsevier : Amsterdam , 2005 .
   Google Scholar
• Krapcho , A. P. Synthetic applications of dealkoxycarbonylation of malonate esters, β-keto esters, α-cyano esters, and related compounds in dipolar aprotic media, part I . Synthesis 1982 , 805 – 822 .
   Google Scholar
• Krapcho , A. P. Synthetic applications of dealkoxycarbonylation of malonate esters, β-keto esters, α-cyano esters, and related compounds in dipolar aprotic media, part II . Synthesis 1982 , 893 – 913 .
   Google Scholar
• Trost , B. M. ; Tamaru , Y. New synthetic reactions—Oxidative decarboxylation . J. Am. Chem. Soc. 1975 , 97 , 3528 – 3530 ; 1977 , 99 , 3101 – 3113 .
   Web of Science ®Google Scholar
• Wladislaw , B. ; Marzorati , L. ; Donnici , C. L. ; Biaggio , F. C. ; Neves , R. M. A. ; Claro Jr. , N. F. PTC sulfanylation of some carboxylic acids derivatives activated by α-sulfonyl or α-sulfinyl group, in solid–liquid system . Phosphorus, Sulfur Silicon Relat. Elem. 1997 , 123 , 197 – 208 .
   Web of Science ®Google Scholar
• Wladislaw , B. ; Marzorati , L. ; DiVitta , C. ; Claro Jr. , N. F. A new methodology for obtaining α-oxo ester equivalents: Sulfanylation of α-sulfonyl carboxylic esters in a solid/liquid phase-transfer catalytic system . Synthesis 1997 , 420 – 422 .
   Google Scholar
• Corey , E. J. ; Lowry , T. H. Stereochemical course of anionic decarboxylation of α-sulfonyl carboxylic acids . Tetrahedron Lett. 1965 , 803 – 809 .
   Google Scholar
• Melo , J. O. F. ; Pereira , E. H. T. ; Donnici , C. L. ; Wladislaw , B. ; Marzorati , L. A novel and easy de-ethoxycarbonylation of α-substituted malonic esters . Synth. Commun. 1998 , 28 , 4179 – 4185 .
   Web of Science ®Google Scholar
• Miles , D. H. ; Chuang , B. S. Reaction of geminal diesters with amine bases 1,5-diazabicyclo[4.3.0]non-5-ene,1,4-diazabicyclo[2.2.2]octane, and 3-quinuclidinol . J. Org. Chem. 1976 , 41 , 208 – 214 .
   Web of Science ®Google Scholar
• Wladislaw , B. ; Marzorati , L. ; Donnici , C. L. New decarboxylation, de-ethoxycarbonylation, and desulfonylation, followed by sulfenylation of some half-esters of malonic acids and α-sulfonylmalonic esters . J. Chem. Soc., Perkin Trans. 1 1993 , 3167 – 3170 .
   Google Scholar
• Bonner , W. A. ; Grimm , R. A. Mechanisms of Raney nickel desulfuration . Org. Sulfur Comp. 1966 , 2 , 35 – 71 .
   Google Scholar
• Shioiri , T. ; Aoyama , T. ; Kuo , Y. C. New methods and reagents in organic synthesis, 26: Reductive desulfonylation of α-sulfonylacetates . Chem. Pharm. Bull. 1982 , 30 , 2787 – 2792 .
   Google Scholar
• Wladislaw , B. ; Marzorati , L. ; Uchoa , R. B. A novel thermal-decomposition of α-methylthiobenzyl phenyl sulfones—Synthesis of para-substituted 1-deuteriobenzaldehydes . Synthesis 1986 , 964 – 965 .
   Google Scholar
• Kamigata , N. ; Suzuki , N. ; Kobayashi , M. Desulfonylation of arylmethane-sulfonyl chlorides catalyzed by dichlorotris(triphenylphosphine)ruthenium(II) . Phosphorus, Sulfur Silicon Relat. Elem. 1984 , 20 , 139 – 144 .
   Web of Science ®Google Scholar
• Kameyama , M. ; Shimezawa , H. ; Satoh , T. ; Kamigata , N. Synthesis of substituted 1,3-dienes by the reaction of alkenesulfonyl chlorides with olefins catalyzed by a ruthenium (II) complex . Bull. Chem. Soc. Jpn. 1988 , 61 , 1231 – 1235 .
   Web of Science ®Google Scholar
• Smith , A. B. ; Hale , K. J. ; McCauley , J. P. An efficient new method for the desulfonylation of β-keto phenylsulfones . Tetrahedron Lett. 1989 , 30 , 5579 – 5582 .
   Web of Science ®Google Scholar
• Lamm , B. ; Ankner , K. Cathodic cleavage of alkyl α-benzenesulfonylcarboxylates . Acta Chim. Scand. B 1978 , 32 , 193 – 196 .
   Google Scholar
• Kunugi , A. ; Abe , K. The cathodic desulfonylation of 1-ethoxycarbonyl-1-(para-tolylsulfonyl)-2-phenylethenes and 1-cyano-1-(para-tolylsulfonyl)-2-phenylethenes at the mercury electrode in nonaqueous solvents. Bull. Chem. Soc. Jpn. 1988, 61, 3329–3331.
   Web of Science ®Google Scholar
• Little , R. D. ; Myong , S. O. Oxidative desulfonylation—Phenyl vinyl sulfone as a ketene synthetic equivalent . Tetrahedron Lett. 1980 , 30 , 3339 – 3342 .
   Web of Science ®Google Scholar
• Julia , M. ; Righini , A. ; Verpeaux , J.-N. Coupling of allylic sulfone with Grignard reagents in presence of copper: Synthesis of olefin . Tetrahedron Lett. 1979 , 29 , 2393 – 2342 .
   Google Scholar
• Chou , T.-S. ; Chang , L.-J. Direct nucleophilic-attack on sulfur atom of a norbornadienyl sulfone . J. Org. Chem. 1985 , 50 , 4998 – 5000 .
   Web of Science ®Google Scholar
• Petrini , M. ; Torregiani , E. TiCl4-promoted addition of nucleophiles to open chain α-amidoalkylphenyl sulfones . Tetrahedron Lett. 2005 , 46 , 5999 – 6003 .
   Web of Science ®Google Scholar
• Wang , J. ; Zhang , Y. The reductive desulfonylation of β-ketosulfones with TiCl4/Sm system . Synth. Commun. 1996 , 26 , 1931 – 1934 .
   Web of Science ®Google Scholar
• Distefano , G. ; Colle , M. D. ; Palo , M. ; Jones , D. ; Bombieri , G. ; Del Pra , A. ; Olivato , P. R. O. ; Mondino , M. G. Experimental and theoretical study of the intramolecular interactions determining the conformation of β-carbonyl sulfoxides . J. Chem. Soc., Perkin Trans. 2 1996 , 1661 – 1669 .
   Google Scholar