Facile rearrangement of O-silylated oximes on reduction with boron trifluoride/borane.
[reaction: see text] Aromatic O-triisopropylsilyl ketoximes were efficiently rearranged to cyclic and acyclic aniline derivatives on reduction with BF3-ethearate/borane. The bulk of the substituents on the silicon atom, the size of the aliphatic ring, and the presence of alkoxy substituents on the aryl group all play an important role in the aniline.
Ortiz-Marciales
Margarita
M
Department of Chemistry, University of Puerto Rico-Humacao, CUH Station, Humacao, Puerto Rico. mr_ortiz@webmail.uprh.edu
Rivera
Luis D
LD
De Jesús
Melvin
M
Espinosa
Sandraliz
S
Benjamin
Josúe A
JA
Casanova
Orlando E
OE
Figueroa
Irving G
IG
Rodríguez
Sheila
S
Correa
Wilbert
W
D000814:Aniline Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D001880:Boranes / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010091:Oximes / Q000737:chemistry*; D013237:Stereoisomerism
D000814:Aniline Compounds; D001880:Boranes; D010091:Oximes; C021274:boron trifluoride; C023650:aniline