Stereochemistry of Dehydrogenation of 1,4,-Cyclohexadiene with 2,3-Dichloro-5,6-dicyano-p-benzoquinone |
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| Authors: | Paul Mü ller,Daniel Joly,Fran ois Mermoud |
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| Affiliation: | Paul Müller,Daniel Joly,François Mermoud |
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| Abstract: | cis- and trans-(3,6-D2)-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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