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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 17, 1987 - Issue 8
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Original Articles

Preparation of α-Diazo-β-Ketosulfones by Diazo-Transfer Reaction with An in situ Generated Azidinium Salt. A Safe and Efficient Procedure for the Diazo-Transfer Reaction in Neutral Medium

Pages 983-992 | Published online: 05 Dec 2006

References

  • Regitz , M. Synthesis , 1972 351 For a review on the diazo-transfer reaction see
  • Hodson , D. , Holt , G. and Wall , D. K. J. Chem. Soc. C , 1968 2201
  • Hua , D. H. , Peacock , N. J. and Meyers , C. Y. 1980 . J. Org. Chem. , 45 : 1717
  • Fridman , A. L. , Andreichikov , Y. S. , Gein , V. L. and Gein , L. F. 1976 . J. Org. Chem. USSR (Engl. Transl.) , 12 : 457
  • Kuo , Y.-C. , Aoyama , T. and Shiori , T. 1982 . Chem. Pharm. Bull. , 30 : 526
  • Balli , H. , Löw , R. , Müller , V. , Rempler , H. and Sezen-Gezgin , A. 1978 . Helv. Chim. Acta , 61 : 97
  • Balli , H. , Müller , V. and Sezen-Gezgin , A. 1978 . Helv. Chim. Acta , 61 : 104
  • Balli , H. and Felder , L. 1978 . Helv. Chim. Acta. , 61 : 108
  • Kokel , B. and Viehe , H. G. 1980 . Angew. Chem. Intern. Ed. , 19 : 716
  • Starting material, m. p. 50–51°, prepared by reaction of levulinic ester ethylerie ketal with the sodium salt of phenylmethyl sulfone in DMSO, followed by acid hydrolysis of the protecting group
  • Starting material, oil, prepared by oxidation of the corresponding sulfide8 with chloroperoxybenzoic acid
  • Hiroi , K. , Matsuda , Y. and Sato , S. Synthesis , 1979 621
  • Starting material, m. p. 71–73°, prepared by oxidation of the corresponding sulfide10 with chloroperoxybenzoic acid
  • Whitner , T. C. Jr. and Reid , E. E. 1921 . J. Am. Chem. Soc. , 43 : 638
  • Starting material, m. p. 12°, prepared by reaction of valeric ester with the sodium salt of phenylmethyl sulfone in DMSO
  • Hazen , G. H. , Weinstock , L. M. , Connell , R. and Bollinger , F. W. 1981 . Syn. Comm. , 11 : 947 For safer alternatives to tosyl azide see

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