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Synthesis and Conformational Properties of the Sterically Crowded D 3d ‐Symmetric all‐ trans Hexa(spirotetrahydrofuranyl)cyclohexane System
Author(s) -
Paquette Leo A.,
Tae Jinsung,
Branan Bruce M.,
Eisenberg Shawn W. E.,
Hofferberth John E.
Publication year - 1999
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/(sici)1521-3773(19990517)38:10<1412::aid-anie1412>3.0.co;2-x
Subject(s) - cyclohexane , hexa , steric effects , chemistry , ion , lithium (medication) , ring (chemistry) , inversion (geology) , ring flip , crystal structure , crystallography , stereochemistry , organic chemistry , geology , psychology , paleontology , structural basin , psychiatry
An unprecedented high barrier to ring inversion [Eq. (1)] prevents 1 from engaging in bifacial complexation with lithium ions. The X‐ray crystal structure analysis of this hexaspiro compound corroborates the adoption of a cyclohexane chair with all six C−O bonds projected equatorially ( 1 ‐eq).