Arsole

Yes, believe it or not, there is actually a molecule

called Arsole... and it's a ring! It is the arsenic
equivalent of pyrrole, and although it is rarely
found in its pure form, it is occasionally seen as a
sidegroup in the form of organic arsolyls. For more
information, see the paper with probably the best
title of any scientific paper I've ever come across:
"Studies on the Chemistry of the Arsoles", G.
Markl and H. Hauptmann, J. Organomet.
Chem., 248 (1983) 269. Although the class of
molecules with this general structure are called
'arsoles', the specific molecule shown on the right
is actually called 'arsenole' (not to be confused
with the London football club, Arsenal). Contrary to
popular belief, new research (see reference below)
shows that arsoles are only moderately aromatic...
Incidentally US patent number US 3 412 119 by
the Dow Chemical Company is entitled 'Substituted
Stannoles, Phospholes, Arsoles, and Stiboles' - I
didn't know there was a substitute for an arsole...
Furthermore, if six of them are bonded together
we can apply the prefix 'sexi', to get 'sexiarsole'.
And the structure where arsole is fused to a
benzene ring is called 'benzarsole'; 6 of these
bonded together would be called 'sexibenzarsole'
(although neither of those sexi- molecules have
been synthesised yet). Another well known
poisonous arsenic molecule is the simple hydride,
called 'arsine', with formula AsH3.
And on a related theme, I've been told of an Aryl
Selenide compound with the superb shorthand of
ArSe, which is both toxic and smelly. The paper it
comes from in J. Am. Chem. Soc. was published by
authors from, of course, the University of Aarhus!
I've been told that it's possible to make molecules
with Se-Se bonds, so if ArSe is bonded to a
selenium halide (with X representing Br, Cl, etc),
then it's possible to make ArSe-SeX. I'll leave this
as a challenge to synthetic chemists to first try to
make this compound, and then to try to get its
name in the title of a paper!
Also, the related molecule phosphole (which just
replaces As with P) is quite amusing if you are a
French speaker, since it's pronounced the same as
'fausse folle'. Fausse means 'fake' or 'false',
and folle means both a 'crazy woman' and a 'drag-
queen' or 'ladyboy'.

Thanks to Neil Brookes, Nicholas Welham, Andy Shipway, Lloyd Evans,

Peter Sims, John Perkins, Bob Buntrock and Ben Mills for some of the
info and details about these molecules. This article inspired Mikael
Johansson from Helsinki University to do a scientific study into the
aromaticity of arsoles, which has been published: Letts. Org.
Chem. 2 (2005) 469. Another intriguing reference supplied by Patrick
Wallace is: G. Mrkl and H. Hauptmann, "Unusual Substitution in an
Arsole Ring", Angew. Chem. Int. Ed. . 11, (1972) 441, and another one
supplied by Simon Cotton is: "Arsole metal complexes", E.W. Abel, I.W.
Nowell, A.G.J. Modinos, C. Towers, J. Chem. Soc., Chem. Commun., (1973)
(7), 258-259. Thanks also to Thomas Jeanmaire and Alan Parker for the
info and translation about phosphole.

Adamantane
 This molecule always brings a smile to the lips of
undergrads when they first hear its name, especially in the
UK. For those not in the know, Adam Ant was an English
pop star in the early 1980's famous for silly songs and
strange make-up. Adamantane actually gets its name from
the Greek adamas meaning 'indestructible', since it's the
chemical building block of diamond.

Bastardane
This is actually a close relative of adamantane,
and its proper name is ethano-bridged
noradamantane. However because it had the
unusual ethano bridge, and was therefore a
variation from the standard types of structure
found in the field of hydrocarbon cage
rearrangements, it came to be known
as bastardane - the "unwanted child". In fact
the original paper had the title "Nonacyclo-
docosane, a Bastard Tetramantane".
A related cage hydrocarbon was
called Golcondane by the first people to synthesis
it in 1993, Mehta and Reddy, in honour of the
400th anniversary of the founding of the Indian
city of Hyderabad, whose ancient name was
Golconda.

A. Nickon and E.F. Silversmith, 'Organic Chemistry: The Name Game',

Pergamon, 1987; P. von R. Schleyer, E., and M.G.B. Drew. J. Am. Chem.
Soc. 90, (1968) 5034.
G. Mehta and S.H.K. Reddy, Angew. Chem., Int. Ed. Engl. 32, (1993)
1160.
 Buckminster Fullerene
This is the famous soccerball-shaped molecule that won
its discoverers the Nobel prize for Chemistry in 1996. It
is named after the architect Buckminster Fuller who
designed the geodesic dome exhibited at Expo '67 in
Montreal, from which Sir Harry Kroto got the idea how 60
Carbon atoms could be arranged in a perfectly
symmetrical fashion. Because the name of the molecule is
a bit of a mouthful, it is often referred to just as a Bucky
Ball. It's also known as 'Footballene' by some researchers.
In fact, there is now a whole 'fullerene zoo', with oddly
coined names, including: Buckybabies (C32, C44, C50,
C58), Rugby Ball (C70), Giant Fullerenes (C240, C540,
C960), Russian Egg or Bucky Onions (balls within
balls), Fuzzyball (C60H60), Bunnyball (C60(OsO4)(4-t-
Butylpyridine)2), Platinum-Burr Ball ({[(C2H5)3P]2Pt}6C60)
and Hetero-fullerenes (in which some Cs are replaced by
other atoms).
There is also a fullerene paper in which the authors
describe a method for severing two adjacent bonds in C60,
entitled "There Is a Hole in My Bucky". And finally,
there's evena village in France called Fulleren, although
it's unrelated to the molecule.

Thanks to A. Haymet for the info regarding footballene, and to Charles Turner for
the names of the other fullerenes which came from: 'Fullerenes', by Robert F. Curl
and Richard E. Smalley, Scientific American October 1991, and to Tom Hawkins for
the JACS reference, and to Patrick Henry for the French village name.

Megaphone
Despite having a ridiculous name, the molecule is quite ordinary. It gets
its name from being both a constituent of Aniba Megaphylla roots and a
ketone.
S.M. Kupchan et al., J. Org. Chem., 43 (1978) 586.