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The effect of pressure on the trimerization and Diels-Alder reaction of cyanoacetylene. Synthesis and reactivity of 2,3,5-tricyanobicyclo[2.2.0]hexa-2,5-diene („tricyano Dewar benzene”)

✍ Scribed by Breitkopf, Volker ;Hopf, Henning ;Klärner, Frank-Gerrit ;Witulski, Bernhard ;Zimny, Bernd

Publisher: John Wiley and Sons
Year: 1995
Tongue: English
Weight: 492 KB
Volume: 1995
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199519950485

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✦ Synopsis

Diels-Alder reactions / 1,2-Dicyano-1,3-~yclobutadiene / Dewar benzenes / High-pressure reactions

The trimerization of cyanoacetylene (la) and the Diels-Alder reaction of l a with 1,3-cyclohexadiene (2) show a powerful pressure-induced acceleration which allows the reaction temperature to be reduced from 1 6 O O C at 1 bar to 40°C at 12 kbar or from 100°C at 1 bar to room temperature at 7 kbar.

At high pressure thermally unstable intermediates like the tricyano Dewar benzene 12 generated in the trimerization of l a or the primary adduct 3a formed in the Diels-Alder reaction of l a with 2 were isolated.

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