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Crown ether catalysed dehydrochlorination of 2-chloro-2-ethynyladamantane (3) with ButOK provided a convenient and efficient method for the synthesis of adamantylidenevinylidene (4). In the presence of olefins (5a–o), compound (4) afforded the corresponding adamantylidenevinylidenecyclopropane derivatives (6a–o) in 30–81% yields.
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Eguchi et al. (1988) studied this question.
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