15482-43-6

Upstream product

• 33739-82-1 6-Hydroxy-1-phenyl-hex-4c-en-1-on 
• 821-06-7 (E)-1,4-dibromobutene 
• 98-86-2 acetophenone 
• 821-09-0 n-Pent-4-enyl alcohol 
• 2100-17-6 4-pentenal 
• 15482-43-6 cis-(2-ethenylcyclopropyl)(phenyl)methanone 
• 21963-38-2 5-vinyl-dihydrofuran-2(3H)-one 
• 41324-11-2 1,4-dihydroxy-hex-5-ene 
• 1393749-79-5 4-hydroxy-1-phenylhex-5-en-1-one 
• 582299-11-4 2-hydroxy-1-phenylhex-5-en-1-one 

Downstream Products

• 56305-38-5 3-Octenyl-phenyl-keton 
• 56305-43-2 (E)-7-Methyl-1-phenyl-octa-4,7-dien-1-one 
• 56305-42-1 (E)-1-phenyldec-4-en-1-one 
• 56305-41-0 (E)-1-phenylhept-4-en-1-one 
• 33524-58-2 cyclopent-3-en-1-yl(phenyl)methanone 
• 120271-01-4 Acetic acid 4-benzoyl-1-methyl-2-vinyl-cyclopentyl ester 
• 120270-91-9 (3-Butoxy-4-vinyl-cyclopentyl)-phenyl-methanone 
• 38376-73-7 1-phenyl-4-hexene-1-one 
• 120271-02-5 4-Benzoyl-2-vinyl-cyclopentanecarboxylic acid methyl ester 
• 15482-43-6 trans-(2-ethenylcyclopropyl)(phenyl)methanone 
• 38376-73-7 (Z)-1-phenylhex-4-en-1-one 
• 38376-74-8 C₁₂H₁₃⁽²⁾HO 

Relevant academic research and scientific papers

Synthesis of 2-Ethenylcyclopropyl Aryl Ketones via Intramolecular SN2-like Displacement of an Ester

The efficient synthesis of trans-2-ethenylcyclopropyl aryl ketones via an intramolecular SN2-like displacement of an allylic ester is reported. A novel 1,5-acyl shift process is also observed that contributes to the product mixture. Theoretical calculations provide a rationale for the observed product ratio.

Photochemical synthesis of highly functionalized cyclopropyl ketones

A series of di- and trisubstituted cyclopropyl ketones 11 were prepared by irradiation of ketones 3 and 5, which bear a leaving group adjacent to the carbonyl C-atom. The required ketones 3 could be easily synthesized either by functionalization of ketones 1 with a hypervalent iodine reagent, 2, or by O-sulfonylation of α-hydroxy ketones 7. The nitrates 5 were obtained by treatment of the corresponding α-bromo ketones with AgNO3. The irradiation of 3 and 5 must be performed in the presence of an acid scavenger (1-methyl-1H-imidazole) to obtain the cyclopropanes 11 in good yields. The synthetic efficiency of the method was, among other things, demonstrated by the preparation of a highly strained bicyclo[2.1.0]pentane 11i in good yield. The mechanism of the photochemical cyclization was investigated by means of photokinetic measurements, as well as by quantum-chemical calculations. It was shown that the presence of the leaving group substantially influences all steps of the photochemical reaction cascade. The X-ray crystal structures of 11j and exo-11k were also determined.

Synthesis of 2-vinylcyclopropane derivatives

2-vinylcyclopropane derivatives has been prepared by treatment of compounds containing two acidic geminal hydrogens with base and 1,4-dibromo-(E)-2-butene.This sequence of reactions for the formation of the cyclopropane ring involves two steps: a) alkylation of a carbanion by 1,4-dibromo-2-butene, and b) intramolecular carbanion addition of the olefinic bond with concerted elimination of bromide anion from the allylic position