Abstract
An angular dibromomethyl group was introduced into 1, 1-dimethyl-1, 2, 3, 4-tetrahydrophenanthren-9-ol (I) by the abnormal Reimer-Tiemann reaction using bromoform. I was converted into bromocyclopropane ketone (III), which had a very high reactivity toward various nucleophiles to give the ring-opened products, having angular formyl group IX, XIX, XX and XXVII, cyanomethyl group XII, sulfonylmethyl group XIII, nitromethyl group XIV, thiomethyl group XVII, and iminomethyl group XVIII. These results suggest that this reaction may be a useful method by angular functionalized methylation for the synthesis of natural products.
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