α‑Diazo-β-ketonitriles: Uniquely
Reactive Substrates for Arene and Alkene Cyclopropanation
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Abstract
An
investigation of the intramolecular cyclopropanation reactions
of α-diazo-β-ketonitriles is reported. These studies reveal
that α-diazo-β-ketonitriles exhibit unique reactivity
in their ability to undergo arene cyclopropanation reactions; other
similar acceptor–acceptor-substituted diazo substrates instead
produce mixtures of C–H insertion and dimerization products.
α-Diazo-β-ketonitriles also undergo highly efficient intramolecular
cyclopropanation of tri- and tetrasubstituted alkenes. In addition,
the α-cyano-α-ketocyclopropane products are demonstrated
to serve as substrates for S<sub>N</sub>2, S<sub>N</sub>2′,
and aldehyde cycloaddition reactions
