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2,4,6-Triisopropylbenzenesulfonyl azide is used as a reagent for diazo transfer to ketones, e.g. under phase-transfer conditions, giving better yields of sterically-hindered ?-diazo ketones than other methods. It is also used for azide transfer to potassium enolates (KHMDS) to form the ?-azido derivatives.
Joshua V. Ruppel.; Rajesh M. Kamble.; X. Peter Zhang. Cobalt-Catalyzed Intramolecular C-H Amination with Arylsulfonyl Azides. Org. Lett. 2007, 9 (23), 4889-4892.
David A. Evans.; Thomas C. Britton. Electrophilic azide transfer to chiral enolates. A general approach to the asymmetric synthesis of .alpha.-amino acids. J. Am. Chem. Soc. 1987, 109 (22), 6881-6883.
Reagent for diazo transfer to ketones, e.g. under phase-transfer conditions, giving better yields of sterically-hindered ɑ-diazo ketones than other methods: Synthesis, 368 (1980); J. Am. Chem. Soc., 102, 6626 (1980); 113, 2598 (1991); Tetrahedron, 43, 5677 (1987).
Also used for azide transfer to potassium enolates (KHMDS) to form the ɑ-azido derivatives: J. Am. Chem. Soc., 109, 6881 (1987); 112, 4011 (1990); Tetrahedron Lett., 28, 6141 (1987). Other bases tend to favor diazo transfer. For further discussion and examples, see: Encyclopedia of Reagents for Organic Synthesis, L. A. Paquette, Ed., Wiley, Chichester (1995), vol. 7, p. 5174.
Hazard Statements: H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P261-P280a-P305+P351+P338-P304+P340-P405-P501a
Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.