Misplaced Pages

1,3-Dehydroadamantane

Article snapshot taken from[REDACTED] with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
(Redirected from 1,3-dehydroadamantane)
1,3-Dehydroadamantane
Names
Preferred IUPAC name Tetracyclodecane
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H14/c1-7-2-9-4-8(1)5-10(9,3-7)6-9/h7-8H,1-6H2Key: YNLPLYJBYLQXCY-UHFFFAOYSA-N
  • InChI=1/C10H14/c1-7-2-9-4-8(1)5-10(9,3-7)6-9/h7-8H,1-6H2Key: YNLPLYJBYLQXCY-UHFFFAOYAN
SMILES
  • C1C2CC34CC1CC3(C2)C4
Properties
Chemical formula C10H14
Molar mass 134.222 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

1,3-Dehydroadamantane or tetracyclodecane 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 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, by reduction of 1,3-dibromoadamantane according to the scheme below:

Scheme 1: 1,3-dehydroadamantane synthesis

Reactions

Oxidation

On standing in solution, it reacts with oxygen from air (with a half-life of 6 hours), yielding a peroxide. The latter converts to a dihydroxide by reaction with lithium aluminium hydride.

Polymerization

Like propellane, 1,3-dehydroadamantane can be polymerized by breaking the axial bond and joining the resulting radicals into a linear chain:

Scheme 2: Polymerization of 1,3-dehydroadamantane.

In this scheme, 1,3-dehydroadamantane is reacted with acrylonitrile in a radical polymerization initiated with lithium metal in tetrahydrofuran. The resulting alternating copolymer has a glass transition temperature of 217 °C

See also

References

  1. Pincock, Richard E.; Torupka, Edward J. (1969). "Tetracyclodecane. Highly reactive 1,3-dehydro derivative of adamantane". J. Am. Chem. Soc. 91 (16): 4593. doi:10.1021/ja01044a072.
  2. Matsuoka, Shin'ichi; Ogiwara, Naoto; Ishizone, Takashi (2006). "Formation of Alternating Copolymers via Spontaneous Copolymerization of 1,3-Dehydroadamantane with Electron-Deficient Vinyl Monomers". J. Am. Chem. Soc. 128 (27): 8708–8709. doi:10.1021/ja062157i. PMID 16819846.
Categories:
1,3-Dehydroadamantane Add topic