Nitrosyl chloride addition to cycloalkenyltrimethylsilanes. An unexpected reversal of regiochemistry of addition, and synthesis of β-aminosilanes

  • Mallya M
  • Nagendrappa G
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Abstract

Cycloalkenyltrimethylsilanes add nitrosyl chloride stereo-and regio-selectively. The addition is syn, with chlorine and nitrosyl group adding to C-1 and C-2 respectively. The products dimerize to diazene dioxides, whose stability depends on the conformational flexibility of the ring-the less flexible are more stable. The less stable adducts convert to oximes and further to 1,2-dichloro-1-nitrosocycloalkanes. The adducts can be hydrolysed to α-chloroketones and reduced to β-aminosilanes. Other interesting observations include transposition of keto group in α-chloroketones and X-ray crystal structure of the amide derivative 6f, which reveals-(CO)-HN…H-CH 2-(CO)-hydrogen contact.

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Mallya, M. N., & Nagendrappa, G. (2007). Nitrosyl chloride addition to cycloalkenyltrimethylsilanes. An unexpected reversal of regiochemistry of addition, and synthesis of β-aminosilanes. Arkivoc, 2006(14), 155–174. https://doi.org/10.3998/ark.5550190.0007.e17

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