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Synthesis and Structural Characterization of Butadienylcalcium‐based Heavy Grignard Reagents and a Ca 4 [O] Inverse Crown Ether Complex
Author(s) -
Wei Baosheng,
Liu Liang,
Zhang WenXiong,
Xi Zhenfeng
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201704176
Subject(s) - chemistry , reagent , halide , crown ether , ether , grignard reaction , iodide , crystal structure , grignard reagent , medicinal chemistry , stereochemistry , organic chemistry , combinatorial chemistry , ion
The structure elucidation of heavy Grignard reagents (RAeX, Ae=Ca, Sr, and Ba, X=halides) has been greatly strived after, mainly because of their inaccessibility and remarkable instability. The synthesis of a series of butadienylcalcium compounds is presented, including 1‐calcio‐4‐lithio‐1,3‐butadiene, 1,4‐dicalcio‐1,3‐butadiene, and a Ca 4 [O] inverse crown ether complex, via the reaction between 1,4‐dilithio‐1,3‐butadienes and calcium iodide in THF. Single‐crystal X‐ray analysis of these unprecedented heavy Grignard reagents revealed unique structural characteristics and bonding modes. Preliminary reaction chemistry was investigated. This study provides a novel class of alkenyl heavy Grignard reagents and a useful synthetic strategy for otherwise unavailable reactive organometallic compounds.