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A Methyl Group Effect on the Conformation of Methylated [3.2]Metacyclophan‐10‐enes
Author(s) -
Grützmacher HansFriedrich,
Neumann Ekkehard
Publication year - 1993
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19931260635
Subject(s) - chemistry , steric effects , stereochemistry , propane , group (periodic table) , methyl group , bridge (graph theory) , ene reaction , medicinal chemistry , organic chemistry , medicine
The syntheses of 7,13‐dimethyl[3.2]metacyclophan‐10‐ene ( 5 ) and 7,10,11,13‐tetramethyl[3.2]metacyclophan‐10‐ene ( 6 ) starting from 1,3‐bis(4‐methylphenyl)propane ( 1 ) are reported. 5 exists in the anti conformation typical of [3.2]metacyclophan‐enes while 6 prefers the syn conformation because of steric repulsion between the methyl groups at the etheno bridge and at the aromatic rings.