Investigation of cyclization methods for a specific compound with acid-catalysts reveals limitations.
Several possible approaches toward effecting the cyclization of 5-isopropyl-3-methyl-2(3-n-pentenyl)-2-cyclohexen-1-one (I) to the decanone (II) are studied. Acid-catalysts, such as polyphosphoric acid and boron trifluoride, are found to be ineffective acting directly on the cyclohexenone. The cyanohydrin of (I) was found to be the unpreferred product in the cyanide reaction, thus eliminating that activated form as a means to effecting the cyclization.
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Robert John Miller (2026) studied this question.
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