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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 21
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Original Articles

Chlorodimethylsulfonium Chloride–Mediated Formation of Phenyl-α-chloroazoalkanes

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Pages 3623-3630 | Received 20 Dec 2007, Published online: 14 Oct 2008

REFERENCES

  • Gaonkar , S. L. ; Rai , K. M. L. A new method for the generation of azoalkenes from ketohydrazones and its application to the synthesis of tetrahydropyridazine derivatives . Tetrahedron Lett. 2005 , 46 , 5969 – 5970 .
  • Wang , Q. R. ; Jochims , J. C. ; Kohlbrandt , S. ; Dahlenburg , L. ; Altalib , M. ; Hamed , A. ; Ismail , A. E. H. 1,2,4-Triazolium salts from the reaction of 1-aza-2-azoniaallene salts with nitriles . Synthesis 1992 , 710 – 718 .
  • Wang , Q. R. ; Liu , X. J. ; Li , F. ; Ding , Z. B. ; Tao , F. G. A facile synthesis of the neutral [1,2,4]triazolo-[3,2-D][1,5]benzoxazepines and their chalcogen-analogues. Synth. Commun. 2002, 32, 1327–1335.
  • Al-Soud , Y. A. ; Shrestha-Dawadi , P. B. ; Winkler , M. ; Wirschun , W. ; Jochims , J. C. 1-Aza-2-azoniaallene salts: reactions with azomethines and other N-nucleophiles . J. Chem. Soc., Perkin Trans. 1998 , 1 , 3759 – 3766 .
  • Wang , Q. R. ; Amer , A. ; Mohr , S. ; Ertel , E. ; Jochims , J. C. [3 + 2]-Cycloadditions of 1-aza-2-azoniaallene cations to multiple bonds . Tetrahedron 1993 , 49 , 9973 – 9986 .
  • MacLeay , R. E. ; Sheppard , C. S. Tertiary-aliphatic amidazo compounds; U.S. Patent 4001207, January 4 , 1977 .
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  • Moon , M. W. The chlorination of aldehyde and ketone phenylhydrazones . J. Org. Chem. 1972 , 37 , 383 – 385 .
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  • Gaonkar and Rai proposed that aryl-α-chloroazoalkanes were formed by reacting arylhydrazones with chloramine-T in refluxing ethanol. However, these products were not isolated, and no characterization data were provided for these compounds . Gaonkar , S. L. ; Rai , K. M. L. A new method for the generation of azoalkenes from ketohydrazones and its application to the synthesis of tetrahydropyridazine derivatives . Tetrahedron Lett. 2005 , 46 , 5969 – 5970 .
  • Brewer , M. Conversion of hydrazones to alkyl chlorides under swern oxidation conditions . Tetrahedron Lett. 2006 , 47 , 7731 – 7733 .
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  • Benzylic arylhydrazones are converted into the corresponding aryl-α-chloroazoalkanes by the procedures developed by Moon; see Ref. 8 and 9 and also Liu , X. ; Liu , Y. ; Wang , Q. ; Zou , J. An efficient approach to the [1,2,4]-triazolo[3,2-d] [1,5]benzoxazepine skeleton—A novel tricyclic ring system . Synth. Commun. 2000 , 30 , 119 – 130 . The conversion of allylic arylhydrazones to allylic aryl-α-chloroazoalkenes has not been reported .
  • O'Connor , R. Tautomerism in phenyl hydrazones . J. Org. Chem. 1961 , 26 , 4375 – 4380 .
  • Yao , H. C. ; Resnick , P. Azo-hydrazone conversion, III: The autoxidation of benzaldehyde phenylhydrazones . J. Org. Chem. 1965 , 30 , 2832 – 2834 .
  • Tiecco , M. ; Testaferri , L. ; Marini , C. S. ; Bagnoli , L. ; Temperini , A. Pyrrolidinamine, peperidinamine and tetrahydropyridazine derivatives from selenium promoted cyclization of alkenyl phenylhydrazones . Tetrahedron 1997 , 53 , 7311 – 7318 .

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