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Efficient α-alkylation and silylation of aromatic O-tert-butyldimethylsilyl ketoximes

✍ Scribed by Margarita Ortiz-Marciales; Melvin De Jesús; Lemuel Quiñones; Dyliana Figueroa; Yadira L. Montes; Carlos Burgos; Benjamin Moctezuma

Book ID
104209638
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
599 KB
Volume
55
Category
Article
ISSN
0040-4020

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✦ Synopsis

The u-alloylation and silylation ofpara substituted acctophenoncs, l-and 2-indanone (O-TBS) oximes at various reaction conditions, were studied. Optimum conversions from 82% to 100% were afforded for the alkylatinn and silylation of these (O-TBS) ketoximes with LDA at -78 °C, using electrophiles, such as, methyl iodide, ethylbromide, benzyl bromide and trimethylchlorosilane.

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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 ox

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