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Practical Procedures for the Preparation of N-tert-Butyldimethylsilylhydrazones and Their Use in Modified Wolff-Kishner Reductions and in the Synthesis of Vinyl Halides and gem-Dihalides

Michael E. Furrow and Andrew G. Myers*

*Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, Email: myerschemistry.harvard.edu

M. E. Furrow, A. G. Myers, J. Am. Chem. Soc., 2004, 126, 5436-5445.

DOI: 10.1021/ja049694s (free Supporting Information)


Abstract

N-tert-butyldimethylsilylhydrazone (TBSH) derivatives from carbonyl-containing compounds serve as superior alternatives to simple hydrazones in Wolff-Kishner-type reduction reactions, in the Barton vinyl iodide preparation, in the synthesis of vinyl bromides, and in the synthesis of gem-diiodides, gem-dibromides, and gem-dichlorides. Optimized procedures are provided for the use of TBSH derivatives in a Wolff-Kishner-type reduction protocol that proceeds at low temperature. Protocols for the use of TBSH derivatives as precursors to vinyl halides and gem-dihalides are described in detail.

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Key Words

Hydrazones, Wolff-Kishner Reduction, Barton vinyl iodide preparation


ID: J48-Y2004-1290