7626-72-4Relevant academic research and scientific papers
Too Short-Lived or Not Existing Species: N-Azidoamines Reinvestigated
Banert, Klaus,Pester, Tom
, p. 4033 - 4039 (2019/04/10)
Treatment of N-chlorodimethylamine with sodium azide in dichloromethane does not lead to N-azidodimethylamine, as thought for more than 50 years. Instead, surprisingly, (azidomethyl)dimethylamine is generated with good reproducibility. A plausible reaction mechanism to explain the formation of this product is presented. The reaction of lithium dibenzylhydrazide with tosyl azide does not result in the creation of an N-azidoamine, which can be detected by IR spectroscopy at ambient temperature, as it was claimed previously. Additional experiments with diazo group transfer to lithium hydrazides show that intermediate N-azidoamines are very short-lived or their formation is bypassed by direct generation of 1,1-diazenes via synchronous cleavage of two N-N bonds.
Palladium-catalysed aminosulfonylation of aryl-, alkenyl- and heteroaryl halides: Scope of the three-component synthesis of N-aminosulfonamides
Emmett, Edward J.,Richards-Taylor, Charlotte S.,Nguyen, Bao,Garcia-Rubia, Alfonso,Hayter, Barry R.,Willis, Michael C.
supporting information; experimental part, p. 4007 - 4014 (2012/06/04)
By using DABCO·(SO2)2, DABSO, as a solid bench-stable SO2-equivalent, the palladium-catalysed aminosulfonylation of aryl-, alkenyl- and heteroaryl halides has been achieved. N,N-Dialkylhydrazines are employed as the N-nucleophiles and provide N-aminosulfonamides as the products in good to excellent yields. The reactions are operationally simple to perform, requiring only a slight excess of SO 2 (1.2-2.2 equiv.), and tolerate a variety of substituents on the halide coupling partner. Variation of the hydrazine component is also demonstrated. The use of N,N-dibenzylhydrazine as the N-nucleophile delivers N-aminosulfonamide products that can be converted into the corresponding primary sulfonamides using a high-yielding, telescoped, deprotection sequence. The ability to employ hydrazine·SO2 complexes as both the N-nucleophile and SO2 source is also illustrated.
