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Stereochemistry of Dehydrogenation of 1,4,-Cyclohexadiene with 2,3-Dichloro-5,6-dicyano-p-benzoquinone

✍ Scribed by Paul Müller; Daniel Joly; François Mermoud

Publisher
John Wiley and Sons
Year
1984
Tongue
German
Weight
438 KB
Volume
67
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

cis‐ and trans‐(3,6‐D~2~)‐1,4‐cyclohexadienes 1a and 1b have been synthesized from cis‐3,4‐dichlorocyclobutene (5). Aromatization to benzene with DDQ is cis‐stereospecific with an uncertainty of 5%. This result is discussed in relation to concerted or stepwise mechanisms for aromatization of 1,4‐dihydroaromatics with 2,3‐dichloro‐5,6‐dicyano‐p‐benzoquinone (DDQ).

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