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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 6, 1976 - Issue 8
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Original Articles

Halothiation as a Method for Oxidation of Primary Halides and Terminal Olefins to Aldehydes

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Pages 575-581 | Received 30 Aug 1976, Published online: 05 Dec 2006

References

  • University Fellow, 1975–1976
  • Kornblum , N. , Jones , W. J. and Anderson , G. J. 1959 . J. Am. Chem. Soc. , 81 : 4113 Recent attention has been given to alkyl halides: B. Ganem and R. K. Boeckman, Jr., Tetrahedron Lett., 917(1974); J. B. Hendrickson and D. D. Sternbach, J. Org. Chem., 40, 3450(1975) and
  • Mura , A. J. Jr. , Majetich , G. , Grieco , P. A. and Cohen , T. 1975 . Tetrahedron Lett. , : 4437 vinyl sulfides: and references contained therein
  • Paquette , L. A. in press . Organic Reactions ,
  • Bohme , H. , Fischer , H. and Frank , R. 1949 . Ann. , 563 : 54 H. Bohme and H. J. Gran, Ann., 581, 133(1953; W. E. Truce, J. H. Birum, and E. T. McBee, J. Am. Chem. Soc., 74, 3594(1952); F. G. Bordwell and B. M. Pitt, J. Am. Chem. Soc., 77, 572(1955); L. A. Paquette, J. Am. Chem. Soc., 86, 4085(1964); L. A. Paquette, L. S. Wittenbrook and K. S. Schreiber, J. Org. Chem., 33, 1080(1968); D. L. Tuleen and V. C. Markum, J. Org. Chem., 32, 204(1967); D. L. Tuleen and D. N. Buchanan, J. Org. Chem., 32, 204(1967); D. L. Tuleen, J. Org. Chem., 32, 4006 (1967); D. L. Tuleen and T. B. Stephans, J. Org. Chem., 34, 31(1969)
  • The authors thank Professor M. S. Newman for a gift of this bromide
  • All new compounds have been characterized spectroscopically and have afforded acceptable (± 0.3%) combustion analyses
  • Bordwell , F. G. , Cooper , G. D. and Morita , H. 1957 . J. Am. Chem. Soc. , 79 : 376 The hydrolysis of halomethyl anyl sulfides has previously been reported: P. G. Gassman and H. R. Drewes, J. Am. Chem. Soc., 96, 3002(1973)
  • Rabilloud , G. 1967 . Bull. Soc. Chim. France , : 384
  • Brook , A. G. , Duff , J. M. , Jones , P. F. and Davis , N. R. 1967 . J. Am. Chem. Soc. , 89 : 431
  • Subsequent to the completion of this work, two reports outlining similar concepts appeared.11 Neither group reported the direct isolation of aldehyde product
  • Mura , A. J. Jr. , Bennett , D. A. and Cohen , T. 1975 . Tetrahedron Lett. , : 4433
  • Bakuzis , P. , Bakuzis , M. L.F. , Fortes , C. C. and Santos , R. 1976 . J. Org. Chem. , 41 : 2769
  • Royals , E. E. and Neal , A. H. 1956 . J. Org. Chem. , 21 : 1448
  • Davies , D. I. , Parfitt , L. T. , Alden , C. K. and Claisse , J. A. 1969 . J. Chem. Soc. (C) , : 1585 Free radical additions of mercaptans to norbornene and related compounds have been previously described
  • By way of contrast, vinyl sulfides are formed predominantly in the analogous preparation of ketones: unpublished results from this laboratory
  • Darzens and Levy . 1937 . Compt. Rend. , 204 : 272

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