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The Dehydrogenation of 1,4-Cyclohexadienes with 2,3-Dichloro-5,6-dicyanobenzoquinone and Triphenylmethylfluoroborate

✍ Scribed by Paul Müller

Publisher
John Wiley and Sons
Year
1973
Tongue
German
Weight
578 KB
Volume
56
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The dehydrogenation of 1,4‐cyclohexadiene (1) cis‐3,6‐dimethyl‐1,4‐cyclohexadiene (2) and trans‐3,6‐dimethyl‐1,4‐cyclohexadiene (3) with triphenylmethylfluoroborate in acetonitrile or 2,3‐dichloro‐5,6‐dicyanobenzoquinone (DDQ) proceeds in the same reactivity sequences 2 > 1 > 3. The mechanism of the dehydrogenation of 1,4‐cyclohexadienes with triphenylmethylfluoroborate and DDQ is discussed in the light of these results and in view of the kinetic isotope effects.

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