ISSN:
0947-3440
Keywords:
Cage compounds
;
Calculations
;
Total syntheses
;
Pyramidalization, olefinic
;
Reactivity
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Homo- and bishomododecahedral cage molecules with one and two O—CO (O—CH2) 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).
Additional Material:
4 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199719971010
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