307520-08-7Relevant articles and documents
Aminocyclodextrins to facilitate the deprotonation of 4-tert-butyl-α- nitrotoluene
Barr, Lorna,Easton, Christopher J.,Lee, Kitty,Lincoln, Stephen F.
, p. 2990 - 2993 (2005)
6A-Amino-6A-deoxy-β-cyclodextrin enhances the rate of the deprotonation of 4-terf-butyl-α-nitrotoluene. The rate constants for reaction of the cyclodextrin-bound species, kinc = 4 × 10-3, 9 × 10-3 and
Continuous Platform to Generate Nitroalkanes On-Demand (in Situ) Using Peracetic Acid-Mediated Oxidation in a PFA Pipes-in-Series Reactor
Tsukanov, Sergey V.,Johnson, Martin D.,May, Scott A.,Kolis, Stanley P.,Yates, Matthew H.,Johnston, Jeffrey N.
supporting information, p. 971 - 977 (2018/08/28)
The synthetic utility of the aza-Henry reaction can be diminished on scale by potential hazards associated with the use of peracid to prepare nitroalkane substrates and the nitroalkanes themselves. In response, a continuous and scalable chemistry platform to prepare aliphatic nitroalkanes on-demand using the oxidation of oximes with peracetic acid and direct reaction of the nitroalkane intermediate in an aza-Henry reaction is reported. A uniquely designed pipes-in-series plug-flow tube reactor addresses a range of process challenges, including stability and safe handling of peroxides and nitroalkanes. The subsequent continuous extraction generates a solution of purified nitroalkane, which can be directly used in the following enantioselective aza-Henry chemistry to furnish valuable chiral diamine precursors with high selectivity, thus completely avoiding isolation of the potentially unsafe low-molecular-weight nitroalkane intermediate. A continuous campaign (16 h) established that these conditions were effective in processing 100 g of the oxime and furnishing 1.4 L of nitroalkane solution.
Conversion of nitroalkanes into carboxylic acids via iodide catalysis in water
Marcé, Patricia,Lynch, James,Blacker, A. John,Williams, Jonathan M. J.
supporting information, p. 1013 - 1016 (2016/01/16)
We report a new method for the conversion of nitroalkanes into carboxylic acids that achieves this transformation under very mild conditions. Catalytic amounts of iodide in combination with a simple zinc catalyst are needed to give good conversions into the corresponding carboxylic acids.
Cinchonidinium acetate as a convenient catalyst for the asymmetric synthesis of cis-stilbenediamines
Walvoord, Ryan R.,Kozlowski, Marisa C.
supporting information, p. 3070 - 3074 (2015/03/04)
Inexpensive and readily available cinchonidinium acetate is an effective catalyst for the syn-selective aza-Henry reaction of arylnitromethanes and aryl imines. The resulting masked cis-stilbenediamine products are produced in excellent diastereoselectivi
Cascade formation of isoxazoles: Facile base-mediated rearrangement of substituted oxetanes
Burkhard, Johannes A.,Tchitchanov, Boris H.,Carreira, Erick M.
supporting information; experimental part, p. 5379 - 5382 (2011/07/08)
Give me five! Nitro compounds and oxetan-3-one react through an intriguing cascade sequence to give isoxazole-4-carbaldehydes using inexpensive reagents in a one-pot procedure (see scheme; Ms=methanesulfonyl). A variety of 3-substituted isoxazole-4-carbaldehydes were obtained in high overall yields.
