Norbornen

Norbornen
Strukturní vzorec
Strukturní vzorec
Model molekuly
Model molekuly
Obecné
Systematický názevbicyklo[2.2.1]hept-2-en
Ostatní názvynorbornylen, norkamfen
Sumární vzorecC7H10
Vzhledbílá pevná látka
Identifikace
Registrační číslo CAS498-66-8
EC-no (EINECS/ELINCS/NLP)207-866-0
PubChem10352
ChEBI52286
SMILESC1=CC2CCC1C2
InChIInChI=1S/C7H10/c1-2-7-4-3-6(1)5-7/h1-2,6-7H,3-5H2
Vlastnosti
Molární hmotnost94,154 g/mol
Teplota tání45 °C (318 K)[1]
Teplota varu96 °C (369 K)[1]
Tlak páry5,22 kPa[1]
Bezpečnost
Teplota vzplanutí−15 °C (258 K)
Není-li uvedeno jinak, jsou použity
jednotky SI a STP (25 °C, 100 kPa).
Některá data mohou pocházet z datové položky.

Norbornen je nenasycený cyklický uhlovodík. Jeho molekula obsahuje cyklohexenový kruh a methylenový můstek mezi atomy uhlíku v polohách 1 a 4. Dvojná vazba v molekule vyvolává silné úhlové napětí a výrazně navyšuje reaktivitu.

Výroba

Norbornen se vyrábí Dielsovou–Alderovou reakcí cyklopentadienu a ethenu; podobně lze získat i řadu substituovaných norbornenů.[2][3] Podobnými bicyklickými sloučeninami jsou norbornadien, který má stejný uhlíkový řetězec, ovšem dvě dvojné vazby, a norbornan, vznikající hydrogenací norbornenu.

Reakce

Norbornen vstupuje do kysele katalyzované hydratační reakce za vzniku norborneolu. Tato reakce posloužila k určení neklasické struktury 2-norbornylového kationtu.

Norbornen se používá v  Catellaniových reakcích a meta-C−H aktivacích.[4]

Některé substituované norborneny se účastní neobvyklých substitučních reakcí za tvorby 2-norbornylového kationtu.

Polynorborneny

Norborneny fungují jako monomery při polymerizacích s otevíráním kruhu. Polynorborneny mívají vysoké teploty skelného přechodu.[5]

Tvorba polynorbornenu polymerizací s otevíráním kruhu

Kromě polymerizací s otevíráním kruhu norbornenové monomery také vstupují do vinylových řetězcových polymerizací.

Podobným monomerem je ethylidennorbornen, odvozený od cyklopentadienu a buta-1,3-dienu.

Reference

V tomto článku byl použit překlad textu z článku Norbornene na anglické Wikipedii.

  1. ↑ a b c https://pubchem.ncbi.nlm.nih.gov/compound/10352
  2. ↑ BINGER, Paul; WEDEMANN, Petra; BRINKER, Udo H. Cyclopropene: A New Simple Synthesis and its Diels-Alder Reaction with Cyclopentadiene. Org. Synth.. Dostupné online. ; Coll. Vol.. S. 231. 
  3. ↑ ODA, Masaji; KAWASE, Takeshi; OKADA, Tomoaki; ENOMOTO, Tetsuya. 2-Cyclohexene-1,4-dione. Org. Synth.. Dostupné online. ; Coll. Vol.. S. 186. 
  4. ↑ Praew Thansandote; Eugene Chong; Kai-Oliver Feldmann; Mark Lautens. Palladium-Catalyzed Domino C−C/C−N Coupling Using a Norbornene Template: Synthesis of Substituted Benzomorpholines, Phenoxazines, and Dihydrodibenzoxazepines. The Journal of Organic Chemistry. 2010-05-21, s. 3495–3498. doi:10.1021/jo100408p. PMID 20423091. 
  5. ↑ Lionel Delaude; Alfred F. Noels. Kirk-Othmer Encyclopedia of Chemical Technology. Weinheim: Wiley-VCH, 2005. ISBN 978-0471238966. doi:10.1002/0471238961.metanoel.a01. Kapitola Metathesis. 

Externí odkazy

  • Obrázky, zvuky či videa k tématu Norbornen na Wikimedia Commons

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