164113-08-0

Upstream product

• 27927-59-9 4-hydroxy-1-phenylpentan-1-one 
• 75-08-1 ethanethiol 
• 1008-76-0 4,5-dihydro-5-phenyl-2(3H)-furanone 

Downstream Products

• 2235-83-8 5-phenyl-2-pentanone 
• 4457-59-4 (2R*,5S*)-2-methyl-5-phenyltetrahydrofuran 

Relevant academic research and scientific papers

Mechanism of the Rearrangement of 2-(Vinyloxy)alkyl to 4-Ketobutyl Radicals

The rearrangement of 2-(vinyloxy)alkyl to 4-ketobutyl radicals has been demonstrated to proceed by a two step mechanism involving initial 5-endo-trigonal cyclization to give a tetrahydrofuranyl radical which then fragments to the final radical.Fragmentation of the tetrahydrofuranyl radicals is demonstrated by their generation from the corresponding 2-(ethylthio)-tetrahydrofurans with stannanes and AIBN.The rearrangement reaction is completely blocked when the intermediate tetrahydrofuranyl radical is set up to undergo a 5-hexenyl rearrangement.