Abstract
The product of the bromination (chlorination) reaction on cis and trans 3-tert-butyl 4-carbomethoxy cyclohexene is studied by nmr. The results show that the reaction of the cis isomer gives 90% of the trans 4-bromo (chloro) cis 3-hydroxy trans 2-tert-butyl cyclohexane 1-carboxylic acid lactone and the reaction of the trans isomer gives trans 1,2-dibromo (dichloro) cis 3-tert-butyl trans 4-carbomethoxy cyclohexane which adopts a twist conformation. For the dibromo compound this kinetic product gives the corresponding thermodynamically more stable isomer, trans 1,2-dibromo trans 3-tert-butyl cis 4-carbomethoxy cyclohexane, by a diotropic rearrangement. The formation of the kinetic product is explained by the reaction of the less stable diaxial conformer of the cyclohexene derivative.
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