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A one-step transformation of aromatic aldehydes to nitriles, using S,S-Dimethylsulfurdiimide as iminating agent. Isolation of dithiatetrazocines as reaction intermediates.

✍ Scribed by Gunda I. Georg; Sarah A. Pfeifer; Manfred Haake


Publisher
Elsevier Science
Year
1985
Tongue
French
Weight
238 KB
Volume
26
Category
Article
ISSN
0040-4039

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✦ Synopsis


z,z-Dimethylsulfurdiimide is explored as a novel and effective reagent for the direct synthesls of aromatic nitriles from aldehydes. A novel eight-membered heterocycle is isolated as a reaction intermediate and a mechanism for this reaction is discussed. Sulfurdiimides 1 belong to a relatively new class of sulfur nitrogen compounds, which have been recognized as valuable intermediates in organic synthesis.' Sulfoximides 2 and sulfilimines 3 have been subject to rather intensive studies, whereas little attention has focused so far on the chemistry of sulfurdiimides.2 However, with the