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8,13‐Dichloro‐1,4‐dimethyl‐9‐(3,5‐dimethylbenzyl)triptycene: Atropisomerism about a C sp 3 CH 2 Bond
Author(s) -
Yamamoto Gaku,
Ōki Michinori
Publication year - 1978
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.197805181
Subject(s) - triptycene , atropisomer , chemistry , group (periodic table) , crystallography , stereochemistry , medicinal chemistry , polymer chemistry , organic chemistry
Atropisomerism about the bond between the triptycene bridgehead and the benzyl group has been observed in compound (1) which contains two Cl and one CH 3 group as peri ‐substituents. ap ‐ (1) and sc ‐ (1) coexist in a 1:2 equilibrium ratio at 80°C; the rotational barrier is 27 kcal/mol. Analogous 9‐benzyltriptycenes with one or two peri ‐substituents have rotational barriers of ca . 13 and ca . 18 kcal/mol, respectively.