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Generation and Reactions of Tetrasubstituted N-Lithiomethyl-succinimides

✍ Scribed by Rainer Schlecker; Dieter Seebach

Publisher
John Wiley and Sons
Year
1977
Tongue
German
Weight
836 KB
Volume
60
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Of the isoelectronic 6‐electron systems 1a, 1b, 1c (Table 1) the deprotonated amides 2 might be useful derivatives for amine acidification (eq. (1)) if the carbonyl group is sterically protected as shown in 3. The tetrasubstituted succinimides 4, 5, 7, 8 and 9 (diacylamines) undergo the reactions (b), (c) and (d) of Scheme 1 with various bases. Besides deprotonation, the ‘self addition’ to give dimers 4b, 5b, 8b and 9b is the most prominent transformation (Table 2). Only in 9 is the steric hindrance to carbonyl addition large enough to get the lithiomethyl‐succinimides 9c in 80% yield (sec.BuLi/THF/HMPT/‐100°) as evidenced by derivatization with alkyl halides, aldehyde, ketones, methyl benzoate, and chloro trimethylsilane (→9d ‐ 9j, Table 3). The possible structures and bonding descriptions for 9c which ‘decomposes’ above −40° are discussed; the acidity of the precursor 9 is shown by equilibration studies to be comparable with that of diphenylmethane.

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