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Tracking the Process of a Solvothermal Domino Reaction Leading to a Stable Triheteroarylmethyl Radical: A Combined Crystallographic and Mass‐Spectrometric Study
Author(s) -
Liu Bin,
Yu Fei,
Tu Min,
Zhu ZhongHong,
Zhang Yuexing,
Ouyang ZhongWen,
Wang Zhenxing,
Zeng MingHua
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201813829
Subject(s) - chemistry , electrospray ionization , methanol , homolysis , bond cleavage , covalent bond , amine gas treating , domino , mass spectrometry , photochemistry , cascade reaction , imine , radical , medicinal chemistry , crystallography , organic chemistry , catalysis , chromatography
A new free carbon radical was obtained in a microwave‐assisted solvothermal reaction of the primary amine (1‐methyl‐1 H ‐benzo[ d ]imidazol‐2‐yl)methanamine with FeCl 3 ⋅6 H 2 O in methanol at 140 °C. Through a combination of crystallography and electrospray ionization mass spectrometry, the reaction process was studied. The longest domino reaction includes 14 steps and forms up to 12 new covalent bonds (9 C−N and 3 C−C bonds) and 3 five‐membered heterocycles. For the first time, the homolytic cleavage of a C−O bond was used to synthesize a triarylmethyl radical.