ChemInform Abstract: Atroposelectivity in the Reactions of ortho‐Lithiated Aromatic Tertiary Amides with Aldehydes.

Bowles, P.; Clayden, Jonathan; Helliwell, Madeleine; McCarthy, Catherine; Tomkinson, M.; Westlund, Neil

doi:10.1002/chin.199751063

ChemInform

1997

DOI: 10.1002/chin.199751063

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ChemInform Abstract: Atroposelectivity in the Reactions of ortho‐Lithiated Aromatic Tertiary Amides with Aldehydes.

P. Bowles¹,

Jonathan Clayden²,

Madeleine Helliwell³

et al.

Abstract: ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

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2012

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“…A natural approach to such a conformational control is to introduce bulky substituents on the phenyl ring, in ortho positions to the urea. The efficiency of this design has been amply demonstrated in the cases of benzamides 43,44 and phenyloxalamides 45 and other aromatic structures. 46 In this article, we show that it is possible to extend this strategy to aromatic bis-ureas and vastly improve the stability of the assemblies.…”

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confidence: 99%

Conformational Control of Hydrogen-Bonded Aromatic Bis-Ureas

et al. 2012

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The phenylurea moiety is a ubiquitous synthon in supramolecular chemistry because it contains strong complementary hydrogen bonding groups and is synthetically very accessible. Here we investigate the possibility to strengthen self-association by conformational preorganization of the phenylurea moiety. In fact, we show that it is possible to strongly enhance intermolecular interactions between hydrogen bonded aromatic bis-ureas by substitution at the ortho positions of the phenylurea groups. Ortho substituents enforce a noncoplanar conformation of the urea and phenyl moieties better suited for hydrogen bonding. Substitution by methyl groups is more efficient than with larger groups, probably because of reduced steric hindrance. These effects have been demonstrated in the case of two different supramolecular architectures, which points to the probable generality of the phenomenon. In addition, this study has led to the discovery of a new bis-urea able to form very stable self-assembled nanotubes in toluene up to high temperatures (boiling point) or low concentrations (10(-7) M) and in chloroform down to 3 × 10(-4) M.

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Conformational Control of Hydrogen-Bonded Aromatic Bis-Ureas

et al. 2012

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ChemInform Abstract: Atroposelectivity in the Reactions of ortho‐Lithiated Aromatic Tertiary Amides with Aldehydes.

Cited by 1 publication

References 1 publication

Conformational Control of Hydrogen-Bonded Aromatic Bis-Ureas

Conformational Control of Hydrogen-Bonded Aromatic Bis-Ureas

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