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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 12
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Original Articles

ortho-(Substituted Silyl)phenylsydnones via a Novel Sydnone to Phenyl Ring, Lithiation-Induced Silicon Migration

Kenneth Turnbull Chemistry Department, Wright State University, Dayton, Ohio, USACorrespondence[email protected]
&
Douglas M. Krein Chemistry Department, Wright State University, Dayton, Ohio, USA
Pages 2061-2067 | Received 03 Oct 2002, Published online: 17 Aug 2006

References

  • Turnbull , K. and Krein , D.M. 1997 . The sydnone ring as an ortho-director of lithiation. Dilithiation of 3-phenylsydnone and trapping by electrophiles . Tetrahedron Lett. , 38 : 1165
  • Turnbull , K. , Sun , C. and Krein , D.M. 1998 . The sydnone ring as an ortho-director of lithiation. 2. Dilithiation of 3-phenylsydnone and regiospecific o-aryl acylation using N-methoxy-N-methylamides . Tetrahedron Lett. , 39 : 1509
  • Turnbull , K. 1985 . J. Bromination of sydnones. I. Reaction with 3-arylsydnones containing electron-donors on the aryl ring . Heterocycl. Chem. , 22 : 965
  • Hodson , S.J. and Turnbull , K. 1985 . J. Bromination of sydnones. II. Bromination of 3-(2-aminophenyl)sydnone and related compounds . Heterocycl. Chem. , 22 : 1223
  • Turnbull , K. 1986 . Debromination of 3-aryl-4-bromosydnones with sodium borohydride . Synthesis , : 334
  • Turnbull , K. , Blackburn , T.L. and Esterline , D.T. 1990 . Bromination of sydnones. III. Bromination of 3-(2-substituted-phenyl)sydnones and subsequent side chain modification . J. Heterocycl. Chem. , 27 : 1259
  • McChord , K.L. , Tullis , S.A. and Turnbull , K. 1989 . Debromination of 4-bromo-3-arylsydnones with sodium sulfite . Synth. Commun. , 19 : 2249
  • Preston , P.N. and Turnbull , K. 1977 . Approaches to the synthesis of compounds containing fused mesoionic rings . J. Chem. Soc., Perkin Trans. 1 , : 1229
  • Burson , W.C., III , Jones , D.R. , Turnbull , K. and Preston , P.N. 1991 . Intramolecular aza-wittig routes to sydnoquinoxalines . Synthesis , : 745
  • Saljoughian , M. and Turnbull , K. 1988 . Acid induced reactions of a sydnone ketoxime . J. Heterocycl. Chem. , 25 : 1817
  • Turnbull , K. and Krein , D.M. 1996 . Formation of 4-hydroxy-4-substituted sydno[3,4-a](4H)indoles via dilithiation of 3-(2-bromophenyl)sydnone . Synthesis , : 1183
  • Gelvin , C.R. and Turnbull , K. 1992 . Sydnones as masked hydrazines for heterocycle formation: reactions of 3-(2-substituted phenyl)sydnones with HCl . Helv. Chim. Acta , 75 : 1931
  • Marx , J.A. and Turnbull , K. 1993 . Formation of 1-bromocarbonylindazoles via cleavage of 4-bromo ortho-substituted arylsydnones with HBr . Tetrahedron Lett. , : 239

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