Gas-phase elimination reactions of deuterium labeled 3-methoxycyclohexenes have been investigated. 1,4-Elimination is heavily favored over 1,2-elimination when strong bases such as hydroxide and amide are used. The 1,2-pathway becomes more competitive when weaker bases such as methoxide are employed, and the mechanism shifts from E1 cB to E2.
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.Acknowl edgement: Support from the National Science Foundation (CHE-8907 198)a nd the donors of the PetroleumR esearchF oundationa rc gratefullya cknowledged.
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