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Borane‐Induced Dimerization of Arylallenes
Author(s) -
Tao Xin,
Daniliuc Constantin G.,
Dittrich Dustin,
Kehr Gerald,
Erker Gerhard
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201808436
Subject(s) - borane , chemistry , substrate (aquarium) , diene , hexa , molar ratio , head (geology) , product (mathematics) , coupling (piping) , coupling reaction , crystallography , stereochemistry , medicinal chemistry , catalysis , materials science , organic chemistry , oceanography , natural rubber , geometry , mathematics , geomorphology , metallurgy , geology
A series of arylallenes react with HB(C 6 F 5 ) 2 in a 2:1 molar ratio to give the tail‐to‐tail 1,6‐diaryl‐2‐boryl‐hexa‐1,5‐diene coupling products. The reaction of the phenylallene substrate with HB(C 6 F 5 ) 2 was shown to initially give the 2‐boryl‐3,4‐diphenyl‐1,5‐hexadiene head‐to‐head coupling product which then rearranged, by a thermally induced Cope rearrangement, into the final product.