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Diorganomagnesium Compounds from Magnesium, Hydrogen, and 1‐Alkenes and Their Application in Synthesis
Author(s) -
Bogdanović Borislav,
Bons Peter,
Konstantinović Stanimir,
Schwickardi Manfred,
Westeppe Uwe
Publication year - 1993
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19931260616
Subject(s) - chemistry , quinuclidine , magnesium , catalysis , hydride , yield (engineering) , magnesium hydride , zirconium , hydrogen , organic chemistry , organometallic chemistry , medicinal chemistry , materials science , metallurgy
1‐Alkenes are converted in high yields to the corresponding primary diorganomagnesium compounds by transition metalcatalyzed hydromagnesation reaction using catalytically prepared suspended (MgH 2 *) or dissolved magnesium hydride (MgH 2 * ). The most active hydromagnesation catalysts have been found to be combinations of zirconium tetrahalides with MgH 2 * or MgH 2 * . The reaction is highly regio‐and chemoselective. The diorganomagnesium compounds prepared in situ from magnesium, hydrogen, and 1‐alkenes can be applied to the synthesis of organic and organometallic compounds just as Grignard compounds (Scheme 3, reaction 3–11). Dioctylmagnesium undergoes the growth reaction with ethene in the presence of quinuclidine and is oxidized by molecular oxygen in high yield to 1‐octanol.