Mechanistic studies of the allylic rearrangements of alpha-silyloxy allylic silanes to silyloxy vinylic silanes.
Mechanistic evidence suggests that the Lewis acid-promoted allylic rearrangement of alpha-silyloxy allylic silanes proceeds along an ionic reaction pathway involving a contact ion pair. The driving force for this transformation is alleviation of steric congestion at the allylic position of the alpha-silyloxy allylic silane and stabilization of pi cc by hyperconjugation.
Kim
Angie I
AI
Department of Chemistry, University of California, Irvine, California 92696-2025, USA.
Kimmel
Kyle L
KL
Romero
Antonio
A
Smitrovich
Jacqueline H
JH
Woerpel
K A
KA
D009682:Magnetic Resonance Spectroscopy; D012821:Silanes / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared
D012821:Silanes