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2005
Substitution reactions
O 0040
Nucleophilic Substitution by Grignard Reagents on Sulfur Mustards. —
thiabicyclononane (I) smoothly undergoes substitution with aromatic, acetylenic,
08- 030 The
and olefinic Grignard reagents as well as primary alkylmagnesium compounds to afford
products of type (III). It proceeds with retention of configuration which confirms a
pathway of neighboring group participation of sulfur. In contrast, the simple thio compounds (IV) and (VII) do not undergo clean substitution. They afford alkylated and/or
brominated products. This indicates that anchimeric assistance is able to direct reaction
outcome towards C-C bond formation. — (CONVERSO, A.; SAAIDI, P.-L.;
SHARPLESS, K. B.; FINN*, M. G.; J. Org. Chem. 69 (2004) 21, 7336-7339; Dep.
Chem., Scripps Res. Inst., San Diego, La Jolla, CA 92037, USA; Eng.) — Jannicke
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