Substitution of HMPT by the cyclic urea DMPU as a cosolvent for highly reactive nucleophiles and bases

Abstract

Abstract The cyclic urea DMPU (N, N′‐dimethyl‐N, N′‐propylene urea = 1,3‐dimethyl‐2‐oxo‐hexahydropyrimidine) is shown to exhibit the same effects HMPT in oxirane‐opening with Li‐acetylide, in a Wittig olefination, in the double deprotonation of nitroalkane, in the Michael addition of Li‐dithiane to cyclohexenone, and in selective generations of certain enolates ( Schemes 1–7 ) DMPU might therefore be as safe substitute of the carcinogenic HMPT as a cosolvent with unique properties in diverse type of reaction.