90112-22-4

Upstream product

• 15121-01-4 1-acetyl-1,2-oxabicyclo<4.1.0>cycloheptane 
• 99572-30-2 2-cyclohexylideneeth-1-yl acetate 
• 1003-64-1 ethylidenecyclohexane 
• 932-66-1 1-cyclohexenyl methyl ketone 

Downstream Products

• 1122-25-4 2-ethylidenecyclohexan-1-one 
• 24337-52-8 (1S,2R)-2-((S)-1-Hydroxy-ethyl)-cyclohexanol 
• 24337-52-8 (1S,2S)-2-((R)-1-Hydroxy-ethyl)-cyclohexanol 
• 108587-13-9 (2R,4S,4aR,8aS)-4-Methyl-2-phenyl-hexahydro-benzo[1,3]dioxine 
• 24337-52-8 (1S,2R)-2-((R)-1-Hydroxy-ethyl)-cyclohexanol 
• 24337-52-8 (1S,2S)-2-((S)-1-Hydroxy-ethyl)-cyclohexanol 
• 2205-25-6 3-methyl-hexahydro-benzofuran-2-one 

Relevant academic research and scientific papers

Preparation of Allylic Acetates from Simple Alkenes by Palladium(II)-Catalyzed Acetoxylation

The scope and limitations of palladium-catalyzed allylic acetoxylation has been investigated, using benzoquinone-manganese dioxide as the reoxidation system.Unsubstituted cycloalkenes gave good to excellent yields of allylic acetates.Total yields were also good for many substituted cycloalkenes and for linear alkenes, but these substrates generally gave several isomeric acetates.The exploratory mechanistic studies show that the acetoxylation can proceed via both 1,2-acetoxypalladation and η3-allylpalladium complex formation.The keen balance between these processes depends on the structure of the alkene.

NEW DEVELOPMENTS OF THE WHARTON TRANSPOSITION

The synthetically useful Wharton transposition can be improved by using a more adequate procedure in the critical step of the intermediate α-epoxyhydrazone cleavage.Either for stable hydrazones or unstable ones, the yield of the transposed allylic alcohol is increased by treatment under anhydrous conditions with highly basic reagents (KDA in the former case, NEt3 in the latter).