2229-00-7

Upstream product

• 930-68-7 cyclohexenone 
• 110-83-8 cyclohexene 
• 67-66-3 chloroform 
• 7664-93-9 sulfuric acid 
• 2228-75-3 (Z)-cyclohex-2-en-1-one oxime 
• 7446-11-9 sulfur trioxide 
• 62-53-3 aniline 

Downstream Products

• 286-18-0 7-azabicyclo[4.1.0]heptane 
• 1541-25-9 3-amino-1-cyclohexene 
• 108-91-8 cyclohexylamine 
• 2228-75-3 (Z)-cyclohex-2-en-1-one oxime 
• 91737-34-7 C₁₃H₁₃ClN₂O₂ 
• 91737-45-0 C₁₃H₁₃ClN₂O₂ 
• 91737-46-1 C₈H₁₂N₂O₂ 
• 91737-35-8 C₈H₁₂N₂O₂ 

Relevant academic research and scientific papers

Electrophilic Epoxidation of α,β-Unsaturated Oximes with Dioxiranes and Ring Opening of the Epoxides

α,β-Unsaturated oximes underwent electrophilic epoxidation with in-situ-generated dimethyldioxirane to give the corresponding epoxides in good yields. This reaction is an example of “carbonyl umpolung” by transformation of α,β-unsaturated ketones to their oximes. Nucleophilic ring-opening reactions of the epoxides afforded α-substituted products. Shi asymmetric epoxidation of the oximes proceeded with moderate enantioselectivity.

Access to Cyanoimines Enabled by Dual Photoredox/Copper-Catalyzed Cyanation of O-Acyl Oximes

An efficient strategy for the synthesis of pharmaceutically important and synthetically useful cyanoimines, as well as cyanamides, has been described. This strategy is enabled by dual photoredox/copper-catalyzed cyanation of O-acyl oximes or O-acyl hydroxamides. This state of the art protocol for cyanoimines and cyanamides features readily available starting materials, mild reaction conditions, good functional group tolerance, and operational simplicity. The resultant cyanoimines can be transformed into structurally diverse and functionally important N-containing heterocycles.

Photochemical Flow Oximation of Alkanes

The nitrosation of several alkanes using tert-butyl nitrite has been performed in flow showing a remarkable reduction in the reaction time compared with batch processing. Due to the necessity for large excesses of the alkane component a continuous recycling process was devised for the preparation of larger quantities of material.

Convenient access to cycloalk-2-enone-derived N -sulfonyl imines

The first synthesis of N-tosyl imines from various cyclopent-2-enones and cyclohex-2-enones was achieved by direct condensation with tosyl amide in the presence of TiCl(OEt)3 and Et3N. In addition, N-tert-butylsulfonyl imines from five- to seven-membered cycloalk-2-enones were obtained through formation of the respective oximes and subsequent Hudson reaction. These compounds are easy to handle solids and they are interesting starting materials for a variety of transformations. Georg Thieme Verlag Stuttgart New York.