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Is 1-acetyl-4-dimethylaminopyridinium acetate an intermediate in the dmap-catalyzed acetylation of tertiary alcohols ?

✍ Scribed by E. Guibe-Jampel; G. Le Corre; M. Wakselman

Book ID: 104237616
Publisher: Elsevier Science
Year: 1979
Tongue: French
Weight: 202 KB
Volume: 20
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)86089-5

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✦ Synopsis

4-

Dimethylaminopyridine (OMAP) is a very efficient acylation catalyst (l-3) particularly for the acetylationof tertiary alcohols (1,3,4). The reaction has been interpreted by the formation of 1-acetyl pyridinium intermediate (3,4,5) and very recently Hbfle has found evidence for the presence of the 1-acetyl-4dimethylaminopyridinium acetate ion pair in solution (3). This prompts us to report our own results on themechanismof the reaction of acetic anhydride with tertbutanol in the presence of DMAP. , Since 1970 we have isolated a series of 1-acyl-4-dimethylaminopyridinium salts (6a-e) and we purpose to compare their reactivities with the DMAP-catalyzed reactions.

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Kinetics of solvolysis of 1-acetyl-4-(1-ethoxycarbonyl-1-cyano) methylene-1,4-dihydroquinoline in undried DMSO-d6· formation of Acetic Anhydride as an intermediate

✍ Leroy H. Klemm; Jennifer J. Lu; Richard A. Klemm 📂 Article 📅 1992 🏛 John Wiley and Sons 🌐 English ⚖ 367 KB

The kinetics of solvolysis of the title compound (QAc) in undried DMSO-ds to give 4-(1ethoxycarbonyl-l-cyano)methylquinoline (QH) and HOAc a t ambient temperature were investigated by 'H nmr spectrometry. With a limited excess of water the solvolysis follows a three-step process of QAc + HzO 3 QH +