1,3-Dehydroadamantane

1,3-Dehydroadamantane
Names
	Preferred IUPAC name Tetracyclo[3.3.1.13,7.01,3]decane
Identifiers
CAS Number	24569-89-9;
3D model ( JSmol)	Interactive image;
ChemSpider	124482;
PubChem CID	141122;
CompTox Dashboard (EPA)	DTXSID40179305 ;
	InChI InChI=1S/C10H14/c1-7-2-9-4-8(1)5-10(9,3-7)6-9/h7-8H,1-6H2 Key: YNLPLYJBYLQXCY-UHFFFAOYSA-N; InChI=1/C10H14/c1-7-2-9-4-8(1)5-10(9,3-7)6-9/h7-8H,1-6H2 Key: YNLPLYJBYLQXCY-UHFFFAOYAN;
	SMILES C1C2CC34CC1CC3(C2)C4;
Properties
Chemical formula	C10H14
Molar mass	134.222 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

1,3-Dehydroadamantane or tetracyclo[3.3.1.1^3,7.0^1,3]decane is an organic compound with formula C₁₀H₁₄, which can be obtained from adamantane by removal of two hydrogen atoms to create an internal bond. It is a polycyclic hydrocarbon, and can be viewed also as being derived from [3.3.1]propellane by addition of a methylene bridge between the two larger rings.

Like other small-ring propellanes, this compound is substantially strained and unstable.

Synthesis

1,3-Dehydroadamantane was obtained in 1969 by Richard Pincock and Edward Torupka,^[1] by reduction of 1,3-dibromoadamantane according to the scheme below: