✦ LIBER ✦

Concerning the formation of magnesium hydride in the preparation of grignard reagents. The origin of 2-methylbenzhydrol in the reaction of methylmagnesium bromide with 2-methylbenzophenone

✍ Scribed by E.C. Ashby; T.L. Wiesemann; J.S. Bowers Jr.; J.T. Laemmle

Book ID: 104212902
Publisher: Elsevier Science
Year: 1976
Tongue: French
Weight: 234 KB
Volume: 17
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)71312-8

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✦ Synopsis

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The reaction of methylmagnesium bromide with aromatic ketones has been the subject of intense mechanistic studies in recent years.2 Since methylmagnesium bromide possesses no S-hydrogen atom, it is incapable of reducing ketones by S-hydrogen reduction and since aromatic ketones possess no o-hydrogen atom, enolization is not possible; thus, only addition product should be obsenred. However, addition of a large excess of methylmagnesium brcunide to aromatic ketones has been shown to give significant yields of aromatic pinacols, 3-5 and hydr01*,~-~ as well as normal 1,2 addition product (eq. 1). The formation of aromatic pinacols has been shown to be 8

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