Chemistry

3D visualization of organic reactions with CAVOC

3D visualization of organic reactions with CAVOC


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Literature example [2] by Brückner et al .: 2,2-bis (trifluoromethyl) ethylene-1,1-dicarbonitrile as a unique enophile

As a continuation of their work described in the literature example [1], Brückner et al. investigated the ene reaction of the enophile 2,2-bis (trifluoromethyl) ethylene-1,1-dicarbonitrile II with a number of other alkenes and published the results in a subsequent article.

Tab. 1
Yields and product ratios for various substituents R1
R.1Yield (III + IV) [%]Product ratio (III: IV)
a-iPr2867 : 33
b-Ph74100 : 0
Tab. 2
Yields for different substituents R2
R.2Yield VI [%]
a-Me96
b-Ph59
Tab. 3
Yields for different substituents R3, R4 and R5
R.3R.4R.5Yield VIII [%]
a-Me-H-H82
b-Ph-H-H23
c-Me-Me-Me84

Information on the literature reaction [2]:

Title:
2,2-bis (trifluoromethyl) ethylene-1,1-dicarbonitrile II as enophile
Abstract:
The ene reaction of various alkenes I, V and VII with the enophile II was investigated. Depending on the structure of the alkenes, the products III / IV, VI and VIII are formed.
Literature:
Brückner, R .; Huisgen, R. (1991):2,2-Bis (trifluoromethyl) ethylene-1,1-dicarbonitrile as a Unique Enophile.. In: J. Org. Chem.. 56(5), 1679-1681


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