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  • Publisher's Accepted Manuscript: Preparation and Characterization of N , N′ ‐Dialkyl‐1,3‐propanedialdiminium Chlorides, N , N′ ‐Dialkyl‐1,3‐propanedialdimines, and Lithium N , N′ ‐Dialkyl‐1,3‐propanedialdiminates
Title: Preparation and Characterization of N , N′ ‐Dialkyl‐1,3‐propanedialdiminium Chlorides, N , N′ ‐Dialkyl‐1,3‐propanedialdimines, and Lithium N , N′ ‐Dialkyl‐1,3‐propanedialdiminates
Abstract

We describe convenient preparations ofN,N′‐dialkyl‐1,3‐propanedialdiminium chlorides,N,N′‐dialkyl‐1,3‐propanedialdimines, and lithiumN,N′‐dialkyl‐1,3‐propanedialdiminates in which the alkyl groups are methyl, ethyl, isopropyl, ortert‐butyl. For the dialdiminium salts, the N2C3backbone is always in thetrans‐s‐transconfiguration. Three isomers are present in solution except for thetert‐butyl compound, for which only two isomers are present; increasing the steric bulk of theN‐alkyl substituents shifts the equilibrium away from the (Z,Z) isomer in favor of the (E,Z), and (E,E) isomers. For the neutral dialdimines, crystal structures show that the methyl and isopropyl compounds adopt the (E,Z) form, whereas thetert‐butyl compound is in the (E,E) form. In aprotic solvents all four dialdimines (as well as the lithium dialdiminate salts) adoptcis‐s‐cisconformations in which there presumably is either an intramolecular hydrogen bond (or a lithium cation) between the two nitrogen atoms.
Authors:
 ;  
Award ID(s):
1954745
Publication Date:
NSF-PAR ID:
10411033
Journal Name:
Helvetica Chimica Acta
Volume:
106
Issue:
5
ISSN:
0018-019X
Publisher:
Wiley Blackwell (John Wiley & Sons)
Sponsoring Org:
National Science Foundation
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