Pyrrole chemistry. XVIII. The thio-Claisen rearrangement

The thio-Claisen rearrangement has been carried out on 2-allylthiopyrrole, l-methyl-2-allylthiopyrrole, and 2,5-diallylthiopyrrole. The products were trapped by acetylation of the β-allyl-α-thiols. Raney nickel desulfurization of these products gave the corresponding β-propylpyrroles but attempts to functionalize the β-allyl group failed. l-Methyl-3-propylpyrrole and 3,4-dipropylpyrrole were also synthesized by other routes for comparison.