Step 1: Preheat the broiler.
Step 2: In a bowl, combine the sugar and cinnamon.
Step 3: Arrange the pineapple on a broiler tray and sprinkle the top with half of the sugar-cinnamon mixture. Broil for 5 minutes, or until the pineapple is lightly browned.
Step 4: Turn the pineapple over, sprinkle with the remaining sugar-cinnamon mixture, and broil for 5 minutes longer, or until lightly browned.
Step 5: Place the broiled pineapple on dessert plates.
Step 6: In a saute pan over medium heat, melt the butter and brown sugar, then cook for 3 minutes. Add the rum and vanilla.
Step 7: Spoon the sauce on the pineapple and serve.
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