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From Pagodanes to Homologous, Non‐Pentagonal Dodecahedranes
Author(s) -
Pinkos Rolf,
Weiler Andreas,
Voss Torsten,
Weber Klaus,
Wahl Fabian,
Melder JohannPeter,
Fritz Hans,
Hunkler Dieter,
Prinzbach Horst
Publication year - 1997
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199719971010
Subject(s) - chemistry , molecule , crystallography , curvature , skeleton (computer programming) , reactivity (psychology) , crystal (programming language) , stereochemistry , organic chemistry , geometry , medicine , mathematics , alternative medicine , pathology , computer science , programming language
Homo‐ and bishomododecahedral cage molecules with one and two OCO (OCH 2 ) linkers installed into the parent pentagonal framework and featuring diverse functionalization patterns have been made available from pagodane precursors via highly expeditious synthetic sequences. The enforced geometrical changes with respect to molecular curvature, olefinic pyramidalization, transannular π,π‐distance as well as to the chemical reactivity particularly of the unsaturated homododecahedranes are generally in good agreement with expectations based on calculations (MM2). In the appreciably pyramidalized monohomododecahedradiene skeleton 40 the non‐parallel π‐bonds are ca. 2.9 (3.1) Å [Φ = ca. 20 (32)°, MM2], in the bishomododecahedradiene skeleton 55 the perfectly syn ‐periplanar π‐bonds 2.81 Å apart (Φ = 18.2°, X‐ray crystal structure).