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Indacyclopentadienes and Aromatic Indacyclopentadienyl Dianions: Synthesis and Characterization
Author(s) -
Zhang Yongliang,
Yang Zhenqiang,
Zhang WenXiong,
Xi Zhenfeng
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201806356
Subject(s) - chemistry , aromaticity , lithium (medication) , ring (chemistry) , crystal structure , medicinal chemistry , stereochemistry , crystallography , molecule , organic chemistry , medicine , endocrinology
A series of unprecedented metallacycles of indium, including indacyclopentadienes ( 2 ), spiro indacyclopentadienes ( 3 ), aromatic indacyclopentadienyl dianions with an In−Li bond ( 4 ), and aromatic indacyclopentadienyl dianions with an In−In bond ( 5 ), were synthesized and structurally characterized by single‐crystal X‐ray structural analysis for the first time. Both indacyclopentadienes 2 and 3 were synthesized by reaction of 1,4‐dilithio‐1,3‐butadienes with InCl 3 . Structural transformations between 2 and 3 were observed. Reduction of indacyclopentadienes 2 with an excess amount of lithium afforded aromatic indacyclopentadienyl dianions 4 with an In−Li bond or 5 with an In−In bond, respectively, depending on the substituents on the ring. The aromatic character of 4 and 5 was confirmed by both experimental measurements and theoretical analysis.