88364-58-3

Upstream product

• 108-24-7 acetic anhydride 
• 119220-61-0 (2S,6S)-2-Methyl-6-trimethylsilanylmethyl-cyclohexanone oxime 
• 75142-63-1 2-<(trimethylsilyl)methyl>cyclohexanone 
• 286-20-4 cyclohexane-1,2-epoxide 
• 131991-79-2 (2RS, 6SR)-6-methyl-2-trimethylsilylmethylcyclohexanone 
• 88364-55-0 (E)-2-trimethylsilylmethylcyclohexanone oxime 
• 131991-79-2 (2RS, 6RS)-6-methyl-2-trimethylsilylmethylcyclohexanone 
• 94142-02-6 (DL)-trans-2-trimethylsilylmethylcyclohexanol 

Relevant academic research and scientific papers

SILICON-DIRECTED BECKMANN FRAGMENTATION

The selective fragmentation reactions of β-trimethylsilylketoximes have been proved to proceed effectively with acid catalysts giving the corresponding nitriles.Cyclic silylketoximes gave unsaturated nitriles.The fragmentation in the Beckmann rearrangement is completely controlled and directed by a trimethylsilyl group to lead the regio- and stereo-specific formation of the double bond.The catalytic fragmentation proceeds with the combination of trimethylsilyl ketoxime acetates and trimethylsilyl trifluoromethanesulfonate giving nitriles in high yields.Excellent stereospecificity of the fragmentation based on the stereochemical outcome was discussed.Simple stereo-controlled synthetic approach to some insect pheromones is also described.

SILICON-DIRECTED BECKMANN FRAGMENTATION. CATALYTIC CLEAVAGE OF CYCLIC β-TRIMETHYLSILYLKETOXIME ACETATES WITH TRIMETHYLSILYL TRIFLUOROMETHANESULFONATE

Cyclic (E)-β-trimethylsilylketoxime acetates were effectively cleaved by a catalytic action of trimethylsilyl trifluoromethanesulfonate to give the corresponding unsaturated nitriles.The fragmentation in the Beckmann rearrangement is completely controlled