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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 3, 1973 - Issue 4
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Original Articles

Reductive Elimination of Bromine from 1,2-Dibromoalkanes Using Organometallic Reagents

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Pages 281-285 | Received 18 Jun 1973, Published online: 05 Dec 2006

References

  • Posner , G. H. Org. Reactions , in press
  • Corey , E. J. and Posner , G. H. 1967 . J. Amer. Chem. Soc. , 89 : 3911 and 90, 5615 (1968);
  • Whitesides , G. M. , Fischer , W. F. Jr. , San Filippo , J. Jr. , Bashe , R. W. and House , H. O. 1969 . ibid. , 91 : 4871
  • Posner , G. H. , Whitten , C. E. and McFarland , P. E. 1972 . J. Amer. Chem. Soc. , 94 : 5106 references therein
  • Posner , G. H. and Sterling , J. J. 1973 . J. Amer. Chem. Soc. , 95 : 3076
  • Singleton , D. M. and Kochi , J. K. 1967 . J. Amer. Chem. Soc. , 89 : 6547 Transition metal promoted 1,2-dehalogenations have been observed: Cr(II)
  • Nozaki , H. , Shirafuji , T. and Yamamoto , Y. 1969 . Tetrahedron , 25 : 3461 CuCl
  • McCutcheon , J. W. 1955 . Org. Syntheses Coll. Vol III , 526 Zn
  • Meriianian , A. , Mayer , T. , Helling , J. F. and Klemick , F. 1972 . J. Org. Chem. , 37 : 3945 Ti:
  • All reactions were performed routinely on a 1–2 mmol scale and in several cases on a 10–15 mmol scale as described previously (cf. ref. 3) with the usual precautions for rigorous exclusion of air and moisture. Cuprous iodide was purchased from Fischer Chemical Co. and was continuously extracted with THF in a Soxhlet extractor for about 12 hr and then dried under vacuum at 25[ddot]; the cuprous iodide thus purified remained pure on standing for several months, and aliquots were used for reaction with organolithium reagents to generate lithium dialkylcuprates(I)
  • Winkler , H. J. S. and Winkler , H. 1967 . Ann. , 705 : 76
  • cis Stilbene is stable under the reaction conditions used
  • 1964 . cf , 42 Dechlorination of 1,2-dichlorocyclohexyl systems is a difficult reaction:. J. F. King and R. G. Pews, Can. J. Chem.,1294
  • Lux , H. and Illman , G. 1958 . Chem. Ber. , 91 : 2143 Chromous perchlorate was prepared according to the procedure of;cf. L. H. Slaugh and J. H. Raley, Tetrahedron, 20, 1005 (1964)
  • Meyer , W. L. and Levinson , A. S. 1963 . J. Org. Chem. , 28 : 2184 See, for example
  • House , H. 0. 1972 . “ Ch. 3 ” . In Modern Synthetic Reactions, , Second ed. New York : W. A. Benjamin .
  • le This dibromoester (le) was prepared in the following way: 10-undecenoic acid → 10,11-dibromoundecanoic acid → 10,11dibromoundecanoyl chloride → 1e
  • Dolezal , S. and Ponert , J. Czechoslovakian Patent 116,3309;Chem. Abstr., 65, 2129e (1966)
  • The authentic sample was prepared by esterification of commercial 10-undecenoic acid (cf. ref. 14)

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