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The Pagodane Route to Dodecahedranes: Total Synthesis and Chemistry of 4,9,14,19‐Tetrasubstituted [1.1.1.1]Pagodanes
Author(s) -
Melder JohannPeter,
Fritz Hans,
Prinzbach Horst
Publication year - 1989
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198903001
Subject(s) - yield (engineering) , cleavage (geology) , ring (chemistry) , chemistry , computational chemistry , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , materials science , physics , thermodynamics , fracture (geology) , composite material
The tetraketone 1 and the dimethoxydiketone 2, R = CH 3 , could prove to be important intermediates en route to dodecahedranes. They can be prepared in several steps in good yield from 7‐ tert ‐butoxynorbornadiene and tetrachlorocyclopentadienone dimethyl ketal. According to force field calculations the four sp 2 ‐hybridized C atoms in 1 should facilitate thermal cleavage of the central four‐membered ring and a subsequent hydrogenation.