Selective Transformation of Well‐Defined Alkenyllithiums to Alkenylmagnesiums via Transmetalation

A series of butadienyl organomagnesium complexes, including 1‐Li‐4‐(MgR)‐butadienes, 1,4‐bis(MgR)‐butadienes, and 1‐Mg‐4‐(MgR)‐butadiene were synthesized starting with 1,4‐dilithio butadienes via the transmetalation reaction between alkenyllithium bond and alkenylmagnesium bond. Single‐crystal X‐ray...

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Bibliographic Details
Published in:Chemistry : a European journal 2018-03, Vol.24 (13), p.3186-3191
Main Authors: Zhu, Miaomiao, Liu, Liang, Zhang, Yongliang, Yu, Hai‐Tao, Zhang, Wen‐Xiong, Xi, Zhenfeng
Format: Article
Language:English
Subjects:
1,4-dilithio-1,3-butadienes
Butadiene
Chemical synthesis
Chemistry
Crystal structure
lithium
magnesium
metallacycles
Structural analysis
transmetalation
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Summary:A series of butadienyl organomagnesium complexes, including 1‐Li‐4‐(MgR)‐butadienes, 1,4‐bis(MgR)‐butadienes, and 1‐Mg‐4‐(MgR)‐butadiene were synthesized starting with 1,4‐dilithio butadienes via the transmetalation reaction between alkenyllithium bond and alkenylmagnesium bond. Single‐crystal X‐ray structural analysis of these butadienyl organomagnesiates revealed unique bonding modes. Study on their structural transformation demonstrated that 1‐Li‐4‐(MgR)‐butadiene is the key intermediate in the reaction process leading to the formation of 1,4‐bis(MgR)‐butadiene and 1‐Mg‐4‐(MgR)‐butadiene. Beautiful butadienes: 1,4‐bis(MgR)‐butadiene, and 1‐Mg‐4‐(MgR)‐butadiene have been synthesized and structurally characterized. The study of mutual transformations reveals that the 1‐Li‐4‐(MgR)‐butadiene is the key intermediate in the formation of the other two organomagnesium complexes.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201704611