Debromination of 4-Bromo-3-Arylsydnones with Sodium Dithionite

References

• Isfahan, , Iran : Department of Medicinal Chemistry, School of Pharmacy, Isfahan University . Permanent address:
   Google Scholar
• Ohta , M. and Kato , H. 1968 . Nonbenzenoid Aromatics , Edited by: Snyder , J. P. 117 – 248 . New York : Academic Press .
   Google Scholar
• Turnbull , K. in press . Synthesis ,
   Google Scholar
• Chung , S. K. and Hu , Q.-Y. 1982 . Synth. Commun. , 12 : 261
   Web of Science ®Google Scholar
• The relatively low yield for aminosydnone (2b) is almost certainly due to the poor solubility of the product (1b) in the extraction solvent, dichloromethane
   Google Scholar
• Norris , R. K. and Smyth-King , R. J. 1982 . Tetrahedron , 38 : 1051
   Google Scholar
• Baker , W. , Ollis , W. D. and Poole , V. D. 1949 . J. Chem. Soc. , : 307
   Web of Science ®Google Scholar
• Hodson , S. J. and Turnbull , K. J. in press . Heterocyclic Chem. ,
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• Ethyl acetate was used as the extraction solvent
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• Esterline , D. , Lowe , J. D. , Turnbull , K. and Wallace , D. the preparation of these sydnones will be reported elsewhere
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• Using one equivalent of sodium dithionite
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• Coburn , R. A. and O'Donnell , J. P. 1972 . J. Org. Chem. , 37 : 1707
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• Even after 3 days with 4 equivalents of sodium dithionite only partial reduction of (2j) occurred (TLC evidence). No attempt was made to isolate the products since a small scale test with sodium borohydride showed that complete reduction to (1j) occurred in a few minutes. Thus, in this case, the latter would be the reagent of choice. It is apparent that reduction with the dithionite is much more sensitive to the steric environment
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• Turnbull , K. 1985 . J. Heterocyclic Chem. , 22 : 965
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• In most cases reaction was complete in under one hour
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