Pagodane

May 31, 2021
If you’ve been to Asia, you might recognize my name.
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Pagodane is a strained, highly symmetrical hydrocarbon. It is so named because its structure resembles that of anAsian pagoda. Its full name is [1.1.1.1]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.

MOTW update

MDMA (3,4-methylenedioxymethamphetamine) was the Molecule of the Week for August 19, 2019. It is a widely abused psychoactive drug known on the street as “ecstasy”. MDMA, however, may have a beneficial use. Jennifer M. Mitchell at the University of California, San Francisco and colleagues there and at several other institutions worldwide report that the drug is efficacious in patients with severe post-traumatic stress disorder (PTSD).Their randomized, double-blind, placebo-controlled phase 3 study was conducted with 90 participants at 15 sites in three countries.

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Pagodane
fast facts

CAS Reg. No. 89683-62-5
SciFinder
nomenclature
2,7,8b,3,4b,6-Ethane-diylidyne-dipentalenol-[1,6-ab:1′,6′-ef]-pentalene, hexadecahydro-
Empirical formula C20H20
Molar mass 260.37 g/mol
Appearance White crystalline solid
Melting point 243 ºC
Water solubility Insoluble
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