74743-50-3

Upstream product

• 3506-54-5 3-(diethylamino)-1-phenylprop-2-en-1-one 
• 13154-14-8 1-propenylmagnesium bromide 
• 123-73-9 trans-Crotonaldehyde 
• 70-11-1 α-bromoacetophenone 
• 123-73-9 crotonaldehyde 
• 98-86-2 acetophenone 
• 3306-07-8 1-benzoyl-2-chloroethene 

Downstream Products

• 58927-85-8 (3Z)-1-phenyl-3-hexen-1-ol 
• 58927-86-9 (E)-1-Phenyl-3-hexen-1-ol 
• 59321-58-3 1-Phenyl-4-hexen-1-ol 
• 1354729-31-9 C₁₉H₂₂O 
• 57542-05-9 (E)-1-phenylhex-4-ene-1-one 

Relevant academic research and scientific papers

Transition-Metal-Free Self-Hydrogen-Transferring Allylic Isomerization

Phenanthroline and tert-butoxide have been established as powerful radical initiators in reactions such as the SRN1-type coupling reactions due to the cooperation of large heteroarenes and a special feature of tert-butoxide. The first phenanthroline-tert-butoxide-catalyzed transition-metal-free allylic isomerization is described. The resulting ketones are key intermediates for indenes. The control experiments rule out the base-promoted allylic anion pathway. The radical pathway is supported by experimental evidence that includes kinetic study, kinetic isotope effect, isotope-labeling experiments, trapping experiments, and EPR experiments.

On tertiary stibine I. Reaction of ω-bromoacetophenone with aldehydes mediated by diphenylantimonyorganometallic reagents

In the presence of diphenylantimonymagnesium, various aldehydes react readily with ω-bromoacetophenone to form α,β-unsaturated ketones in good yields.

Reaction of α-Halogeno Ketones with Carbonyl Compounds Promoted by CeI3, CeCl3-NaI,or CeCl3-SnCl2

Reaction of α-halogeno ketones with aldehydes in the presence of CeI3 in tetrahydrofuran is found to give α,β-unsaturated ketones in excellent yields under mild conditions.In contrast, treatment of α-halogeno ketones and carbonyl compounds with CeCl3-NaI or CeCl3-SnCl2 affords β-hydroxy ketones in good yields.It is assumed that these reactions proceed via cerium enolates.The combined reagents, however, cannot be applied to a Reformatsky-type reaction.Regiospecific and aldehyde chemoselective aldol synthesis are also described.

Carbon-Carbon Bond Formation between α-Halogenoketones and Aldehydes Promoted by Cerium(III) Iodide or Cerium(III) Chloride-Sodium Iodide

α-Halogenoketones react with aldehydes to form α,β-unsaturated ketones accompanied by dehalogenation in the presence of cerium(III) iodide, but the use of cerium(III) chloride-sodium iodide results in the formation of β-keto alcohols.