Abstract
Reactions of 1-bromo-6-(2-hydroxyethoxy)cyclohexene ( 2) and its chloro analog 3 with potassium t-butoxide in dimethyl sulfoxide at 60–70° gave cyclohex-2-enone ethylene ketal ( 7) and cis-2,5-dioxabicyclo[4.4.0]dec-7-ene ( 8) as the major products. Under these conditions, 1-(2-hydroxyethoxy)-1,4-cyclohexadiene ( 13) is also converted to 7 and elimination products, benzene and ethylene glycol. Conversion of 13 to 7 was shown to be reversible by examination of 7 that had been treated with t-BuOK. in DMSO- d 6. In tetrahydrofuran, 2 and t-BuOK gave benzene as a major product, together with small amounts of 2,5-dioxabicyclo[4.4.0]-dec-6-ene ( 6), 7, and 8. Mechanisms are proposed for these substitution reactions.
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