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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Rutherford on January 03, 2014, 07:42:30 AM

Title: Adamantane IUPAC
Post by: Rutherford on January 03, 2014, 07:42:30 AM

Why is adamantane (http://www.drugbank.ca/drugs/DB03627/structure?dim=3d) called Tricyclo[3.3.1.1]decane?
Trycyclo- is because three cycles form adamantane (the "4^th" is produced from the three).
Why is [3.3.1.1] in the brackets? Could someone mark the bridges in adamantane to which these numbers belong?

Title: Re: Adamantane IUPAC
Post by: sjb on January 03, 2014, 08:20:49 AM

See e.g. http://dx.doi.org/10.1351/pac199971030531

Title: Re: Adamantane IUPAC
Post by: kriggy on January 03, 2014, 09:18:57 AM

Its tricyklo[3.3.1.1^3.7]decane
3.3.1.1 means number of carbons in that cycle 3 means 3 carbons in that cycle and 1 means amount of carbons in bridge. The carbons where the 1st bridge connects doesnt count.
hope this image helps
(https://www.chemicalforums.com/proxy.php?request=http%3A%2F%2Fi.imgur.com%2F3Mm0liB.png%3F1&hash=7c44140cada28059ca0efc88ec069d660e8c9a14)
and btw there is no 4th cycle.

Title: Re: Adamantane IUPAC
Post by: Rutherford on January 03, 2014, 10:20:47 AM

Okay, thanks.