74457-57-1

Basic information

• Product Name: 1-acetoxy(methyl)-2,2-difluoro-3-phenylcyclopropane
• CAS NO: 74457-57-1
• Molecular Weight: 226.223
• Mol File: 74457-57-1.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 1-acetoxy(methyl)-2,2-difluoro-3-phenylcyclopropane(CAS DataBase Reference)
• NIST Chemistry Reference: 1-acetoxy(methyl)-2,2-difluoro-3-phenylcyclopropane(74457-57-1)
• EPA Substance Registry System: 1-acetoxy(methyl)-2,2-difluoro-3-phenylcyclopropane(74457-57-1)

Safety Data

• Hazardous Substances Data: 74457-57-1(Hazardous Substances Data)

Upstream product

• 77134-01-1 (Z)-cinnamyl acetate 
• 1895-39-2 sodium chlorodifluoroacetate 
• 1504-58-1 3-Phenyl-2-propyn-1-ol 
• 4510-34-3 (Z)-cinnamyl alcohol 
• 680-15-9 2,2-difluoro-2-(fluorosulfonyl)acetate 

Downstream Products

• 118138-22-0 2,2-difluoro-1-hydroxy(methyl)-3-phenylcyclopropane 
• 81635-10-1 C₁₆H₁₄F₂O₂S 
• 81735-94-6 (1E,3Z)-3-Fluoro-4-phenyl-1,3-butadienylphenylsulfon 
• 81635-19-0 (1E,3,E)-3-Fluoro-4-phenyl-1,3-butadienylphenylsulfone 
• 118138-28-6 Methanesulfonic acid (1R,3S)-2,2-difluoro-3-phenyl-cyclopropylmethyl ester 

Relevant articles and documents

Evaluating the thermal vinylcyclopropane rearrangement (VCPR) as a practical method for the synthesis of difluorinated cyclopentenes: Experimental and computational studies of rearrangement stereospecificity

Vinyl cyclopropane rearrangement (VCPR) has been utilised to synthesise a difluorinated cyclopentene stereospecifically and under mild thermal conditions. Difluorocyclopropanation chemistry afforded ethyl 3-(1'(2'2'-difluoro-3'-phenyl)cyclopropyl) propenoate as all four stereoisomers (18a, 18b, 22a, 22b) (all racemic). The trans-E isomer (18a), prepared in 70% yield over three steps, underwent near quantitative VCPR to difluorocyclopentene 23 (99 %). Rearrangements were monitored by 19F NMR (100-180 °C). While cis/trans cyclopropane stereoisomerisation was facile, favouring trans-isomers by a modest margin, no E/Z alkene isomerisation was observed even at higher temperatures. Neither cis nor trans Z-alkenoates underwent VCPR, even up to much higher temperatures (180 °C). The cis-cyclopropanes underwent [3,3]-rearrangement to afford benzocycloheptadiene species. The reaction stereospecificity was explored by using electronic structure calculations, and UB3LYP/6-31G methodology allowed the energy barriers for cyclopropane stereoisomerisation, diastereoisomeric VCPR and [3,3]-rearrangement to be ranked in agreement with experiment.