What molecule am I?
Pagodane is a strained, highly symmetrical hydrocarbon. It is so named because its structure resembles that of anAsian pagoda. Its full name is [220.127.116.11]pagodane, and it belongs to the D2h point symmetry group.
Horst Prinzbach and colleagues at the University of Freiburg (Germany) and Ciba-Geigy (Basel, Switzerland) reported the synthesis of pagodane in 1987. According to the authors, “The synthesis of [pagodane] commences from isodrin1 and consists of ≈45 functional and structural modifications which are efficiently concentrated into 14 one-pot operations with an overall yieldof 24%.” The yield is amazingly high for such a complex synthesis.
Pagodane’s empirical formula, C20H20, is isomeric with that of dodecahedrane, the Molecule of the Week for February 22, 2021. Prinzbach and his coauthors anticipated that pagodane and its derivatives could be isomerized to the dodecahedrane structure.2 Yields were low at first, but they achieved suitable conversions from pagodane precursors by 1997.
Pagodane is not an article of commerce, so no hazard information is available for it. Similar compounds are considered to be nonhazardous except for possible low-level aquatic toxicity.
1. Isodrin is a hexachlorinated hydrocarbon and a now-banned insecticide.
2. Leo Paquette and co-workers at Ohio State University (Columbus) prepared dodecahedrane via a 29-step synthesis in 1982.
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Pagodane fast facts
|CAS Reg. No.||89683-62-5|
|Molar mass||260.37 g/mol|
|Appearance||White crystalline solid|
|Melting point||243 ºC|
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