Journal article

Dimethyl cis- and trans-1, 2-dimethyl-cyclohexane-1, 2-dicarboxylate

ID Rae, AK Serelis

Australian Journal of Chemistry | Published : 1990


L- Methoxy-3-trimethylsilyloxybuta-l, 3-diene adds readily to dimethylmaleic anhydride, and the product can be converted into dimethyl cis-1, 2-dimethylcyclohex-4-ene-l, 2-dicarboxylate (3). The several steps required mean that this route compares unfavourably with direct addition of butadiene to the anhydride. The best route to the cis-diester (3) is cyclialkylation of the dianion from dimethyl 2, 3-dimethylbutanedioate with (Z)-1, 4-dichlorobut-2-ene. A bismethylation reaction is used to prepare imide (11), which can be converted into the cis-diester (1) only with considerable difficulty, and bismethylation of the dianion formed from dimethyl cis-cyclohex-4-ene-l, 2-dicarboxylate gives mai..

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