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Steric and electronic effects on the reduction of O-silylated aromatic ketoximes with borane

✍ Scribed by Margarita Ortiz-Marciales; Dyliana Figueroa; José A López; Melvin De Jesús; Rafael Vega

Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 235 KB
Volume: 41
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)01109-6

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✦ Synopsis

4-Methoxy acetophenone oximes substituted at the oxygen with TMS, TBS, TIPS and MDPS groups were reduced with borane±THF obtaining the 4-methoxy-N-ethyl aniline as the principal product, up to a 95% yield in the case of the more hindered TIPS group. The 2-methoxy-and 2,4-methoxyacetophenone O-TBS oximes produced only the rearranged secondary aniline. Reduction of 1-indanone O-TBS oximes aorded only the tetrahydroquinoline, whereas the 2-indanone analog provided only 2-aminoindan.

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