[3 + 2]-Cycloadditions of nitrile ylides after photoactivation of vinyl azides under flow conditions

• Stephan Cludius-Brandt,
• Lukas Kupracz and
• Andreas Kirschning

Beilstein J. Org. Chem. 2013, 9, 1745–1750, doi:10.3762/bjoc.9.201

• the first photochemical transformation of vinyl azides to pyrrole derivatives under continuous-flow conditions. Only recently, we reported the two-step preparation of vinyl azides 1 in mircrostructured flow reactors starting from alkenes 6, using the solid-phase bound iodine azide transfer-reagent 7

Multistep flow synthesis of vinyl azides and their use in the copper-catalyzed Huisgen-type cycloaddition under inductive-heating conditions

• Lukas Kupracz,
• Jan Hartwig,
• Jens Wegner,
• Sascha Ceylan and
• Andreas Kirschning

Beilstein J. Org. Chem. 2011, 7, 1441–1448, doi:10.3762/bjoc.7.168

• vinyltriazoles is reported. The synthesis relies on a stable polymer-bound equivalent of iodine azide that serves to carry out 1,2-functionalization of alkenes in a telescope flow protocol. The intermediate 2-iodo azides are subjected to a DBU-mediated polymer-supported elimination step yielding vinyl azides in

• reactor. Keywords: flow reactor; inductive heating; iodine azide; polymer-supported reagents; vinyl azides; Introduction Azides are highly versatile organic functional groups and their preparation and their reactivity are well explored [1]. In contrast, the synthesis of vinyl azides is far away from

• process for the generation of vinyl azides 4 is the two-step protocol developed by Hassner et al. [9] through the in situ reaction of sodium azide with iodine chloride in dichloromethane or another polar solvent (Scheme 1). Thus, it includes the generation of hazardous and highly explosive iodine azide

A short synthesis of (±)-cherylline dimethyl ether

• Bhima Y. Kale,
• Ananta D. Shinde,
• Swapnil S. Sonar,
• Bapurao B. Shingate,
• Sanjeev Kumar,
• Samir Ghosh,
• Soodamani Venugopal and
• Murlidhar S. Shingare

Beilstein J. Org. Chem. 2009, 5, No. 80, doi:10.3762/bjoc.5.80

• group was confirmed by its IR spectroscopy in which the peak at 1715 cm−1 was observed. Radical azidonation of aldehyde 7 with iodine azide generated in situ by the reaction of sodium azide with ICl) at room temperature gave an acyl azide and subsequent Curtius rearrangement provided isocyanate 10 in

Controlling hazardous chemicals in microreactors: Synthesis with iodine azide

• Johan C. Brandt and
• Thomas Wirth

Beilstein J. Org. Chem. 2009, 5, No. 30, doi:10.3762/bjoc.5.30

• Johan C. Brandt Thomas Wirth Cardiff University, School of Chemistry, Park Place, Cardiff CF10 3AT, UK. 10.3762/bjoc.5.30 Abstract Aromatic aldehydes have been converted into the corresponding carbamoyl azides using iodine azide. These reactions have been performed safely under continuous flow

• other functional groups [5]. Iodine azide is a very hazardous but valuable reagent that is easier and much more safely handled under microreactor conditions. Iodine azide is a solid compound, highly explosive and toxic. It is known to add stereospecifically to carbon–carbon double bonds with high

• regioselectivity following an ionic mechanism. This azido-iodination reaction is by far the most common synthetic application of iodine azide [6][7][8][9][10][11][12][13][14]. Due to the weakness of the iodine–nitrogen bond iodine azide also reacts in a radical manner upon heating, where this weak bond can be