Uranium metallacycle ((Me sub 3 Si) sub 2 N) sub 2 UCH sub 2 SiMe sub 2 NSiMe sub 3 : A mild reagent for the synthesis of methyl ketones from nitriles

Journal Article · Fri Jul 21 04:00:00 EDT 1989 · Journal of Organic Chemistry; (USA)

DOI:https://doi.org/10.1021/jo00276a046· OSTI ID:7196875

Dormond, A; Elbouadili, A; Moise, C ^[1]

---

1. Faculte des Sciences, Dijon (France)

The reaction of nitriles with Grignard reagents is a widely applicable synthetic route to ketimines, which by facile hydrolysis give ketones. However, this reaction suffers some limitations. With aliphatic nitriles, a serious complication arises due to the acidity of the {alpha}-hydrogen atom. If strongly basic solvents are used, they compete with the nitrile in formation of an organomagnesium complex. If organolithium reagents are used instead of Grignard reagents, the greater basicity of both lithium reagent and the product ketimine salt causes even more difficulty. We report here a specific, rapid, clean, and high-yield reaction of nitriles to give the corresponding methyl ketones by using the uranium metallacycle 1 in nonbasic solvents.

• OSTI ID: 7196875
• Journal Information: Journal of Organic Chemistry; (USA), Journal Name: Journal of Organic Chemistry; (USA) Vol. 54:15; ISSN JOCEA; ISSN 0022-3263
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ACTINIDE COMPOUNDS
DATA
DATA ANALYSIS
EXPERIMENTAL DATA
INFORMATION
KETONES
MEASURING INSTRUMENTS
MEASURING METHODS
NITRILES
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANOMETALLIC COMPOUNDS
SYNTHESIS
URANIUM COMPOUNDS