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A Convergent Route to Enantiomerically Pure Higher [ n −2]Triangulanedimethanol Derivatives and [ n ]Triangulanes ( n ≥7)
Author(s) -
de Meijere Armin,
Khlebnikov Alexander F.,
Kozhushkov Sergei I.,
Miyazawa Kazutoshi,
Frank Daniel,
Schreiner Peter R.,
Rinderspacher B. Christopher,
Yufit Dmitrii S.,
Howard Judith A. K.
Publication year - 2004
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.200461166
Subject(s) - rotation (mathematics) , chemistry , mathematics , scheme (mathematics) , power (physics) , crystallography , thermodynamics , materials science , physics , mathematical analysis , geometry
Remarkably high specific rotations, even at 589 nm, are exhibited by the enantiomerically pure σ‐[9]helicenes ( M )‐(−)‐ and ( P )‐(+)‐[9]triangulanes (see scheme). This significant power of rotation, which is in very good agreement with calculated values, must be attributed to the rigid helical framework of σ bonds in these formally saturated hydrocarbons.