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Angewandte Chemie International Edition in English

Volumn 28, Issue 8, 1989, Pages 1044-1047

A New Coordinating Chiral Lithium Amide

(7) Barr, Donald b Berrisford, David J a Jones, Raymond V H c Slawin, Alexandra M Z d Snaith, Ronald b Stoddart, J Fraser a Williams, David J d

a UNIVERSITY OF SHEFFIELD (United Kingdom)

b University Chemical Laboratories (United Kingdom)

c ZENECA Grangemouth Works (United Kingdom)

d IMPERIAL COLLEGE LONDON (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84990165959 PISSN: 05700833 EISSN: 15213773 Source Type: Journal
DOI: 10.1002/anie.198910441 Document Type: Article

Times cited : (29)

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- n
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- 2 shows a contrasting aabb pattern scattered around mean NLi bond lengths (Fig. 2) that correspond with those reported.

81
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- 2 symmetry (IV). In the dimers III and IV, the two homotopic amide ligands contain, respectively, homotopic and diastereotopic 5‐membered chelate rings. The coordination geometries and ring distortions are at present being investigated by ab initio and MO calculations on model systems in collaboration with Dr. D. R. Armstrong (University of Strathclyde, UK). (Formula Presented.)

82
- 84990088473
- 3) reveals a single lithium amide species at ambient temperature which persists on cooling down to −90°C. A minor component is also observed in a proportion of < 5% which is independent of concentration (0.062‐0.206 M) and temperature. This is unequivocally the parent amine (R, R)‐1 resulting from partial hydrolysis of the lithium amide during the experiments. No spectroscopic evidence for constitutional isomerism or aggregation equilibria is observed. We thank Dr. D. Reed (SERC NMR Service, University of Edinburgh) for his assistance in obtaining some of these spectra.

83
- 84990152852
- 2 in benzene in the concentration range 0.07‐0.12 M to give a supramolecular mass of 551 ± 12, i.e. n = 1.90 ± 0.04. The slight variance from n = 2.0 cannot arise from an amidolithium dimer‐monomer equilibrium since this would be concentration dependent. The low value can be attributed to partial hydrolysis to the parent amine (R,R)‐1 prior to or during the measurement (see Ref. [39]).

84
- 84990139802
- n in toluene/HMPA. An internal enolate quench with trimethylsilyl chloride gives (R)‐4‐tert butyl‐1‐[(trimethylsilyl)oxy]cyclohexene in 84% enantiomeric excess.

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