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“Dichloroneopentylsilaethene” 1 reacts with naphthalene in a surprising [4 + 2] cycloaddition to give the endo product 2. This can be reduced with LiAlH4 to afford 3, which was analyzed by X-ray crystallography. A reaction of 1 with cyclohexa-1,3-diene forms bicyclic silacyclobutanes in a [2 + 2] cycloaddition.
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Auner et al. (1991) studied this question.
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