Three Component Reactions. XX. Methoxymercuration of Cyclohexa‐1,4‐dienes.
The methoxymercuration of several cyclohexa‐1,4‐dienes leads to insoluble mixtures of mono‐ and bismercuricompounds 2–4 and 5–7. After reduction with NaBH4/NaOH mixtures of methoxycyclohexenes and bismethoxycyclohexanes result. The result of capillary gaschromatographic analyses and n.m.r. spectra allow a semiquantitative evaluation of the reaction pathways.
Composition of Mixtures of Hydrocarbons after BIRCH‐Reduction of Substituted Benzenes and Acid Catalyzed Addition of Alcohols to Alkylsubstituted Cyclohexenes and Cyclohexa‐1,4‐dienes.
10 different benzene hydrocarbons 1, indane, tetraline, anisol and phenol are reduced by sodium in liquid ammonia in the presence of methanol to the BIRCH products 2. The product mixture compositions are determined through capillary GLC. On storage at + 6°C some rearomatization of the 1,4‐cyclohexadienes 2 occurs. Data of the 1H‐ and 13C‐n.m.r. spectra and also mass spectra of the BIRCH 1,4‐dienes 2 are given. For comparison 4‐alkoxycyclohexenes 4 and 1‐alkoxy‐1‐methylcyclohexanes 8 are prepared and spectroscopically characterized. Acid‐catalyzed addition of alcohols to the 1,4‐cyclohexadiene systems is a slow process and gives the 4‐alkoxy‐4‐alkylcyclohex‐1‐enes (4) only in moderate yields up to 30 %. Most of the products are dimers 5 and also oligomers 6 of the parent hydrocarbons 2.
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The chlorination of the title compound (I) in the presence of the alcohols (IIa), (IIb) or AcOH (IIc) under known conditions gives rise to a mixture of the products (III)‐(VIII) which is analyzed by GLC.
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