Radical ring closures of 4-isocyanato carbon-centered radicals.
The 2-(2-isocyanatophenyl)ethyl radical was generated from the corresponding bromide with tributyltin and tris(trimethylsilyl)silyl radicals and shown to ring close in the 6-endo-mode to afford 3,4-dihydro-1H-quinolin-2-one as the major product. Cyclization in the 5-exo-mode to produce 2,3-dihydroindole-1-carbaldehyde, after hydrogen abstraction, was a minor reaction. Rate constants for the two processes were estimated and compared with reaction enthalpies computed by the DFT method.
Minin
Patricia L
PL
School of Chemistry, University of St. Andrews, St. Andrews, Fife, KY16 9ST, UK.
Walton
John C
JC