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15N NMR study of dialkyl, N-alkyl-N′-phenyl and diphenyl sulphur diimides: Assignment of configuration in solution

✍ Scribed by Bernd Wrackmeyer; Christian Köhler; Max Herberhold

Publisher
John Wiley and Sons
Year
1993
Tongue
English
Weight
306 KB
Volume
31
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

^15^N NMR spectra of dialkyl sulphur diimides (1) [R^1^(NSN)R^2^; R^1^ = R^2^ = Me (a), Et (b), ^n^Pr (c), ^i^Pr (d), ^n^Bu (e), ^t^Bu (f), ^t^Oct (g)], N‐alkyl‐N′‐phenyl sulphur diimides (2) [R^1^(NSN)R^2^; R^1^ = Me (a), Et (b); R^2^ = Ph] and diphenyl sulphur diimide (3) were measured at variable temperature. The assignment is based on the comparison with data for the corresponding N‐sulphinylamines R^1^(NSO). The Z/E configuration is always preferred at low temperature, whereas the minor isomer adopts the Z/Z configuration. In the presence of bulky substituents (If and g), only the isomer with Z/E configuration is observed. At room temperature, ^15^N NMR signals were not observed for symmetrically substituted sulphur diimides, but a single averaged ^14^N resonance can be measured. The unsymmetrically substituted sulphur diimides 2a and b adopt the Z/E configuration with the alkyl group Z and the phenyl group E. There are no indications of other isomers at low temperature. ^14^N NMR spectra at room temperature prove that the (Z)‐phenyl/(E)‐alkyl isomer contributes little to the equilibrium.

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