ChemInform Abstract: BIS(METHOXYCARBONYL)SULFUR DIIMIDE, A CONVENIENT REAGENT FOR THE ALLYLIC AMINATION OF ALKENES

Kresze, G.; MUENSTERER, H.

doi:10.1002/chin.198413125

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■ Experimental Section1

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2018

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“…The material obtained from this method provided an identical 1 H NMR spectrum to previous report. 59 An image of the 1 H NMR spectrum is supplied in the Supporting Information. The data provided here is for comparison to the 15 Using a known diazotransfer procedure, 60 the product was isolated (24 mg) in 44% yield.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Evidence for a Sigmatropic and an Ionic Pathway in the Winstein Rearrangement

et al. 2018

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The spontaneous rearrangement of allylic azides is thought to be a sigmatropic reaction. Presented herein is a detailed investigation into the rearrangement of several allylic azides. A combination of experiments including equilibrium studies, kinetic analysis, density functional theory calculations, and selective N-isotopic labeling are included. We conclude that the Winstein rearrangement occurs by the assumed sigmatropic pathway under most conditions. However, racemization was observed for some cyclic allylic azides. A kinetic analysis of this process is provided, which supports a previously undescribed ionic pathway.

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Section: ■ Experimental Sectionmentioning

confidence: 99%