Tetrahedron Letters p. 4867 - 4870 (1982)
Update date:2022-08-29
Topics:
Newcomb, Martin
Burchill, Michael T.
Lithium N-butyl-4-pentenylamide (1) in tetrahydrofuran at 22 deg C rearranged smoothly to give a mixture (after protonation) of 1-butyl-2-methylpyrrolidine, formed by an unusual cyclization process, and cis- and trans-N-butyl-pentenylamine; in the presence of 2.0 molar equiv of hexamethylphosphoramide, the total rate of isomerization was accelerated by a factor of 2.5.
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