Stereochemistry of Dehydrogenation of 1,4,‐Cyclohexadiene with 2,3‐Dichloro‐5,6‐dicyano‐p‐benzoquinone
- 1 February 1984
- journal article
- research article
- Published by Wiley in Helvetica Chimica Acta
- Vol. 67 (1) , 105-112
- https://doi.org/10.1002/hlca.19840670113
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).Keywords
This publication has 36 references indexed in Scilit:
- Intermediates in the Dehydrogenation of Hydroaromatic Compounds with QuinonesHelvetica Chimica Acta, 1983
- Ein einfacher Weg zutrans-3,4-DihalocyclobutenSynthesis, 1981
- Stereochemistry of 1,4-conjugate elimination reactionsJournal of the American Chemical Society, 1978
- meso-Dihydroanthracene chemistry. Synthesis and mechanistic information. 1,4-Conjugate eliminationsAccounts of Chemical Research, 1971
- Kinetics and mechanism of the pyrolysis of 1,3-cyclohexadiene. Thermal source of cyclohexadeienyl radicals and hydrogen atoms. Addition of hydrogen atoms to benzene and tolueneJournal of the American Chemical Society, 1967
- Dehydrogenation Mechanisms. On the Mechanism of Dehydrogenation of Acenaphthene by QuinonesJournal of the American Chemical Society, 1967
- Nuclear Magnetic Resonance Studies of 1,3-Butadienes. I. The Spectra of Halogenated ButadienesJournal of the American Chemical Society, 1965
- Cyclobutadiene- and Benzocyclobutadiene-Iron Tricarbonyl Complexes1Journal of the American Chemical Society, 1965
- Untersuchungen in der Cyclobutanreihe, XI. Über die stereoisomeren Cyclooctatetraen‐dichloride und das cis‐3.4‐Dichlor‐cyclobutenEuropean Journal of Inorganic Chemistry, 1964
- Mechanisms of Elimination Reactions. XIII. 1,4-Conjugate Eliminations. I. Some meso-Dihydroanthracene Derivatives2Journal of the American Chemical Society, 1955