1,3-Dehydroadamantane

1,3-Dehydroadamantane.svg 150px Tetracyclo[3.3.1.13,7.01,3]decane 24569-89-9 correct FDA 4RDA4M7V9J 141122 124482 C1C2CC34CC1CC3(C2)C4 1/C10H14/c1-7-2-9-4-8(1)5-10(9,3-7)6-9/h7-8H,1-6H2 YNLPLYJBYLQXCY-UHFFFAOYAN 1S/C10H14/c1-7-2-9-4-8(1)5-10(9,3-7)6-9/h7-8H,1-6H2 YNLPLYJBYLQXCY-UHFFFAOYSA-N 10 14 1,3-Dehydroadamantane or tetracyclo[3.3.1.13,7.01,3]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, Richard E. Pincock Edward J. Torupka 1969 Tetracyclo[3.3.1.13,7.01,3]decane. Highly reactive 1,3-dehydro derivative of adamantane J. Am. Chem. Soc. 91 16 4593 10.1021/ja01044a072 by reduction of 1,3-dibromoadamantane according to the scheme below: thumb|none|400px|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 [1.1.1]propellane, 1,3-dehydroadamantane can be polymerized by breaking the axial bond and joining the resulting radicals into a linear chain: thumb|none|400px|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 Shin'ichi Matsuoka Naoto Ogiwara Takashi Ishizone 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 10.1021/ja062157i 16819846 See also [1.1.1]Propellane [2.2.2]Propellane References Category:Adamantanes Category:Cyclopropanes