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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 25, 1995 - Issue 1
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Original Articles

The In Situ Generation and Use of Iodomethyllithium for the One-Carbon Homologation of Boronic Esters and Epoxide Formation from Carbonyl Compounds

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Pages 127-133 | Received 16 May 1994, Published online: 23 Sep 2006

References

  • Brown , H. C. , Singh , S. M. and Rangaishenvi , M. V. 1986 . J. Org. Chem. , 51 : 3150 For a paper which compares a variety of methods available for the one-carbon homologation of boronic esters, see:
  • Sadhu , K. M. and Matteson , D. S. 1985 . Organometallics , 4 : 1687
  • Michnick , T. J. and Matteson , D. S. 1991 . Syn. Lett. , : 631
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  • Koebrich , G. and Von Nagel , R. 1970 . Chem.-Ztg., Chem. App. , 94 : 984 For the initial report on the preparation of ICH2Li, see:
  • van Eikema Hommes , N. J. R. , Bickelhaupt , F. and Klumpp , G. W. 1987 . Recl. Trav. Chim. Pays-Bas , 106 : 514 For other papers dealing with the preparation and use of ICH2Li, see:
  • Kobayashi , T. and Pannell , K. H. 1991 . Organometallics , 10 : 1960
  • Burger , U. and Huisgen , R. 1970 . Tetrahedron Lett. , : 3057 The mono-Grignard of methylene iodide is known, see:
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  • Villiéras , J. 1967 . Bull. Soc. Chim. Fr. , : 1520 Diiodomethyllithium has also been employed synthetically, see:
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  • Andersen , M. W. , Hildebrandt , B. , Köster , G. and Hoffmann , R. W. 1989 . Chem. Ber. , 122 : 1777
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  • Kauffmann , T. , König , R. and Wensing , M. 1984 . Tetrahedron Lett. , 25 : 637 The use of triphenylsilyl- and triphenylgermyl-iodomethyllithium for the preparation of triphenylsilyl- and triphenylgermyl-substituted epoxides from carbonyl compounds has been reported, see:
  • Lipton , M. , Sorensen , C. M. and Sadler , A. C. 1980 . J. Organomet. Chem. , 186 : 155

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