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Filtering by: Advisor White, James D. Subject Aromatic compounds -- Synthesis

Tandem intramolecular photocycloaddition-retro-Mannich fragmentation as a route to indole and oxindole

Creator:

Li, Yang

Abstract:

Irradiation of a tryptamine linked through its side-chain nitrogen to an alkylidene malonate residue results in an intramolecular [2 + 2] cycloaddition to the indole 2,3-double bond. The resultant cyclobutane undergoes spontaneous retro-Mannich fission to produce a spiro[indoline-3,3-pyrrolenine] with relative configuration defined by the orientation of substituents in the transient...

Resource Type:

Dissertation