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Propylmagnesium bromide, butadiene, and catalytic amounts of [(PPh3)2NiCl2] afford octa-2,7-dienyl-magnesium bromide; this cyclises to cis-(2-vinylcyclo-pentyl)methylmagnesium bromide, which can be thermally epimerised to the trans isomer.
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Felkin et al. (1975) studied this question.
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