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Original Articles

SYNTHESIS AND REACTIONS OF 2-(HYDROXYIMINO)-2-PHENYLETHYL ARENEDITHIOCARBOXYLATES. A NEW SYNTHESIS OF 2,4-DIARYLTHIAZOLES

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Pages 135-140 | Received 17 Sep 1984, Accepted 21 Nov 1984, Published online: 13 Dec 2006

References

  • Kato , S. , Sugino , K. , Matsuzawa , Y. , Katada , T. , Noda , I. , Mizuta , M. , Goto , M. and Ishida , M. 1981 . Liebigs Ann. Chem. , : 1798
  • Kato , S. , Chiba , S. , Goto , M. , Mizuta , M. and Ishida , M. 1982 . Synthesis , : 457
  • Ishida , M. , Sato , H. and Kato , S. 1982 . Synthesis , : 927
  • Ohta , M. and Sugiyama , M. 1963 . Bull. Chem. Soc. Jpn. , 36 : 1437 From cyanomethyl dithiobenzoate;
  • Gotthardt , H. and Christl , B. 1968 . Tetrahedron Lett. , : 4743 From carboxybenzyl dithiobenzoate;
  • Kato , S. , Yamamoto , S. , Ando , K. , Itoh , K. , Mizuta , M. and Ishida , M. 1981 . Z. Naturforsch. , 37b : 739
  • Kato , S. , Mitani , T. and Mizuta , M. 1973 . Int. J. Sulfur, Chem. , 8 : 359 8. 2-Chloroacetophenone oxime 2, was prepared from 2-chloroacetophenone and hydroxylamine hydrochloride by modified method of M. Masaki et al., 11 (79%, m.p. 85–87°C)
  • Karabatsos , G. J. , Taller , R. A. and Vane , F. M. 1963 . J. Am. Chem. Soc. , 85 : 2326
  • In the absence of triphenylphosphine dibromide, the oxime 3, was completely recovered even in refluxing conditions
  • Masaki , M. , Fukui , K. and Ohta , M. 1967 . J. Org. Chem. , 32 : 3564 The reaction between triphenylphosphine dibromide and acetophenone oxime derivatives under similar conditions gave the corresponding imidoyl bromides 7, or keteneimines 8, in moderate yields;
  • Dubs , P. and Stuessi , R. 1976 . Synthesis , : 696
  • Wiley , R. H. , England , D. C. and Behr , L. C. 1951 . Org. React. , 6 : 367
  • Fenselau , A. H. , Hamamura , E. H. and Moffatt , J. G. 1970 . J. Org. Chem. , 35 : 3546 The cyclization reaction may occur from the anti isomer. Syn-anti isomerization of oximes under the similar conditions has been reported;, P. Blumbergs, C. B. Thanawalla, A. B. Ash. C. N. Lieske and G. M. Steinberg, J. Org. Chem., 36, 2023 (1971)
  • The formation of triphenylphosphine oxide and sulfur was detected by TLC analyses
  • Funke , E. , Huisgen , R. and Schaefer , F. C. 1971 . Chem. Ber. , 104 : 1550

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