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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”︁)
Author(s) -
Breitkopf Volker,
Hopf Henning,
Klärner FrankGerrit,
Witulski Bernhard,
Zimny Bernd
Publication year - 1995
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199519950485
Subject(s) - chemistry , cyanoacetylene , hexa , benzene , reactivity (psychology) , diels–alder reaction , medicinal chemistry , diene , organic chemistry , computational chemistry , stereochemistry , catalysis , molecule , medicine , natural rubber , alternative medicine , pathology
The trimerization of cyanoacetylene (1a) and the Diels‐Alder reaction of 1a with 1,3‐cyclohexadiene (2) show a powerful pressure‐induced acceleration which allows the reaction temperature to be reduced from 160°C at 1 bar to 40°C at 12 kbar or from 100deg;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 1a or the primary adduct 3a formed in the Diels‐Alder reaction of 1a with 2 were isolated.