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To make the clementine jelly, put the sugar, vanilla pod, cinnamon stick, clementine juice and 100ml water in a large pan and bring to a gentle simmer. Meanwhile, peel the clementines and remove all the pith and outside membranes. Put the broken-up segments into a bowl and pour over the spiced sugar syrup. Cover with cling film and allow to macerate for at least 30 mins.
Meanwhile, cut the madeira cake into 2cm-thick slices, trimming off and discarding the dark edges. Divide the slices between 12 glasses and push down in an even layer. Soak the gelatine leaves in cold water.
Drain the clementines, pouring the liquid into a small saucepan. Discard the vanilla and cinnamon stick. Divide the clementines between the glasses in an even layer. Gently warm the liquid. Once it is warm, squeeze the gelatine to remove the excess water and stir into the warm liquid until completely melted.
Pour a layer of the jelly over the clementines. Transfer the pots to the fridge and allow to set for at least 3 hrs.
To make the chocolate layer, heat the cream to just below boiling. Remove from the heat, add the chocolate and stir until melted and smooth. Add the liqueur and butter and mix until fully combined. Pour into a jug and allow to cool for 15-20 mins. Pour on top of the jelly and put back in the fridge for a few hours to set.