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By R Alan Jones; Gerritt P Bean

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3 (Continued) N-Vinylpyrroles Obtained from Ketoximes No. 5979 [163] No. 3 (Continued) N-Vinylpyrroles Obtained from Ketoximes No. 3 (Continued) N-Vinylpyrroles Obtained from Ketoximes No. 3 (Continued) N-Vinylpyrroles Obtained from Ketoximes Structure Yield (%) Bp, °C/torr (Mp, °C) d 420 nD20 References 1 2 3 4 5 6 7 78 n-Pr 16 – 40 40–62/5 No. 3 (Continued) N-Vinylpyrroles Obtained from Ketoximes No. 3 (Continued) N-Vinylpyrroles Obtained from Ketoximes No. 3 (Continued) N-Vinylpyrroles Obtained from Ketoximes No.

The reaction is efficiently catalyzed by potassium, rubidium, and tetrabutylammonium hydroxides. It should be noted that the last two bases have a selective effect on the construction of the tetrahydroindole ring (synthesis of 4,5,6,7-tetrahydroindole) [196], while KOH, as it was already discussed earlier, is also active in the vinylation step. For the reaction of cyclohexanone oxime with acetylene, it has been established that the most effective polar solvents in this reaction is DMSO, and the system DMSO–dioxane is the most efficient of the mixed solvents [159].

However, the comparison of yields of both compounds under similar conditions allows to assume [161] that the preparation of N-vinyl-4,5,6,7-tetrahydroindole in a one step does not exclude its direct synthesis by the interaction of acetylene with any reactive intermediate (since the yield of N-vinyl-4,5,6,7-tetrahydroindole is always appreciably higher than that of 4,5,6,7-tetrahydroindole). According to the mechanism proposed in the first communications dedicated to this reaction, 3H-pyrrole A can serve as an intermediate of this type.

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