Editing Diamondoid (section)

==Examples==
 
[[File:Diamondoids.png|center|400px|Diamondoids, from left to right [[adamantane]], [[diamantane]], [[triamantane]] and one isomer of [[tetramantane]]]]

Examples include:
* [[Adamantane]] (C<sub>10</sub>H<sub>16</sub>)
* [[Iceane]] (C<sub>12</sub>H<sub>18</sub>)
* BC-8 (C<sub>14</sub>H<sub>20</sub>)
* [[Diamantane]] (C<sub>14</sub>H<sub>20</sub>) also ''diadamantane'', two face-fused cages
* Triamantane (C<sub>18</sub>H<sub>24</sub>), also ''triadamantane''. Diamantane has four identical faces available for anchoring a new C<sub>4</sub>H<sub>4</sub> unit.
* Isotetramantane (C<sub>22</sub>H<sub>28</sub>). Triamantane has eight faces on to which a new C<sub>4</sub>H<sub>4</sub> unit can be added resulting in four [[isomer]]s. One of these isomers displays a helical twist and is therefore [[prochiral]]. The [[Axial chirality|''P'' and ''M'']] [[enantiomer]]s have been separated.
* Pentamantane has nine isomers with chemical formula C<sub>26</sub>H<sub>32</sub> and one more pentamantane exists with chemical formula C<sub>25</sub>H<sub>30</sub>
* Cyclohexamantane (C<sub>26</sub>H<sub>30</sub>)<ref>{{cite journal |first1=J. E. P. |last1=Dahl |first2=J. M. |last2=Moldowan |first3=T. M. |last3=Peakman |first4=J. C. |last4=Clardy |first5=E. |last5=Lobkovsky |first6=M. M. |last6=Olmstead |first7=P. W. |last7=May |first8=T. J. |last8=Davis |first9=J. W. |last9=Steeds |first10=K. E. |last10=Peters |first11=A. |last11=Pepper |first12=A. |last12=Ekuan |first13=R. M. K. |last13=Carlson | title= Isolation and Structural Proof of the Large Diamond Molecule, Cyclohexamantane (C<sub>26</sub>H<sub>30</sub>) | journal= Angewandte Chemie International Edition | year= 2003 | volume= 42 | pages= 2040–2044 |doi= 10.1002/anie.200250794 | pmid= 12746817 | issue= 18}}</ref>

* Super-adamantane (C<sub>30</sub>H<sub>36</sub>)

One tetramantane isomer is the largest ever diamondoid prepared by [[organic synthesis]] using a keto-[[carbenoid]] reaction to attach cyclopentane rings.<ref>{{cite journal | title=A New Approach to the Construction of Diamondoid Hydrocarbons. Synthesis of ''anti''-Tetramantane |last1=Burns |first1=W. |last2=McKervey |first2=M. A. |last3=Mitchell |first3=T. R. |last4=Rooney |first4=J. J. | journal= Journal of the American Chemical Society | volume=100 |issue=3 | pages=906–911 |year=1978 | doi=10.1021/ja00471a041}}</ref> Longer diamondoids have been formed from diamantane dicarboxylic acid.<ref>{{cite journal | journal= Angewandte Chemie International Edition | date= Mar 25, 2013 |volume=52 |issue=13 | pages=3717–3721 | title=Evidence of diamond nanowires formed inside carbon nanotubes from diamantane dicarboxylic acid |last1=Zhang |first1=J. |last2=Zhu |first2=Z. |last3=Feng |first3=Y. |last4=Ishiwata |first4=H. |last5=Miyata |first5=Y. |last6=Kitaura |first6=R. |last7=Dahl |first7=J. E. |last8=Carlson |first8=R. M. |last9=Fokina |first9=N. A. |last10=Schreiner |first10=P. R. |last11=Tománek |first11=D. |last12=Shinohara |first12=H. | pmid=23418054 | doi=10.1002/anie.201209192}}</ref> The first-ever isolation of a wide range of diamondoids from petroleum took place in the following steps:<ref name="Dahl"/> a [[vacuum distillation]] above 345&nbsp;°C, the equivalent [[atmospheric boiling point]], then [[pyrolysis]] at 400 to 450&nbsp;°C in order to remove all non-diamondoid compounds (diamondoids are thermodynamically very stable and will survive this pyrolysis) and then a series of [[high-performance liquid chromatography]] separation techniques.

In one study a tetramantane compound is fitted with [[thiol]] groups at the bridgehead positions.<ref>{{cite journal|title=Functionalized Nanodiamonds Part 3: Thiolation of Tertiary/Bridgehead Alcohols|first1= Boryslav A.|last1= Tkachenko|first2= Natalie A.|last2= Fokina|first3= Lesya V.|last3= Chernish|first4= Jeremy E. P.|last4= Dahl|first5= Shenggao|last5= Liu|first6= Robert M. K.|last6= Carlson|first7= Andrey A.|last7= Fokin|first8= Peter R.|last8= Schreiner|journal= Organic Letters |date=2006 |volume=8 |issue=9 |pages= 1767–70|doi=10.1021/ol053136g |pmid= 16623546}}</ref> This allows their anchorage to a [[gold]] surface and formation of [[self-assembled monolayer]]s (diamond-on-gold).

Organic chemistry of diamondoids even extends to ''pentamantane''.<ref>{{cite journal | last1 = Fokin | first1 = Andrey A. | last2 = Schreiner | first2 = Peter R. | last3 = Fokina | first3 = Natalie A. | last4 = Tkachenko | first4 = Boryslav A. | last5 = Hausmann | first5 = Heike | last6 = Serafin | first6 = Michael | last7 = Dahl | first7 = Jeremy E. P. | last8 = Liu | first8 = Shenggao | last9 = Carlson | first9 = Robert M. K. | year = 2006 | title = Reactivity of [1(2,3)4]Pentamantane (Td-Pentamantane): A Nanoscale Model of Diamond | journal = The Journal of Organic Chemistry | volume = 71 | issue = 22| pages = 8532–8540 | doi = 10.1021/jo061561x | pmid = 17064030 }}</ref> The medial position (base) in this molecule (the isomer [1(2,3)4]pentamantane) is calculated to yield a more favorable [[carbocation]] than the apical position (top) and simple [[bromination]] of pentamantane ''1'' with [[bromine]] exclusively gives the medial bromo derivative ''2'' which on hydrolysis in water and [[dimethylformamide|DMF]] forms the [[Alcohol (chemistry)|alcohol]] ''3''.

[[File:PentamaneChemistry.png|center|400px|Pentamane chemistry]]

In contrast [[nitrooxylation]] of ''1'' with [[nitric acid]] gives the apical [[nitrate]] ''4'' as an intermediate which is hydrolysed to the apical [[Alcohol (chemistry)|alcohol]] ''5'' due to the higher [[steric hindrance|steric demand]] of the active [[electrophilic]] {{chem|NO|2|-}}{{chem|HNO|3|+}} species. This alcohol can react with [[thionyl bromide]] to the bromide ''6'' and in a series of steps (not shown) to the corresponding [[thiol]]. Pentamantane can also react with [[tetrabromomethane]] and [[Quaternary ammonium cation|tetra-''n''-butylammonium]] bromide (TBABr) in a [[free radical reaction]] to the bromide but without selectivity.