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

Helvetica Chimica Acta - Tập 65 Số 1 - Trang 385-391 - 1982
T. Mukhopadhyay1, Dieter Seebàch1
1Laboratorium für Organishe Chemie der Eidgenössischen Technischen Hochschule, Eth‐Zentrum, Universitätstrasse 16, CH‐8092 Zürich

Tóm tắt

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.

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