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The Pagodane Route to Dodecahedranes: Dodecahedradienes—Unusually “Pyramidalized”, Isolable Olefins
Author(s) -
Melder JohannPeter,
Pinkos Rolf,
Fritz Hans,
Prinzbach Horst
Publication year - 1990
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.199000951
Subject(s) - sn2 reaction , thermal decomposition , double bond , decomposition , chemistry , oxygen , stereochemistry , photochemistry , crystallography , polymer chemistry , organic chemistry
The highly strained, extremely energy‐rich dodecahedradienes 2 and 3 with plane‐parallel CC double bonds are accessible by thermolysis of the bislactone 1 and via the S N 2 variant of the pagodane‐dodecahedrane route, respectively. Owing to strong “pyramidalization” these dienes are extremely sensitive to oxygen, but thermally very stable. Both can be hydrogenated to dedecahedrane.