72174-84-6

Upstream product

• 141-97-9 ethyl acetoacetate 
• 75326-15-7 (2-bromo-1-phenylethyl)dimethylsulphonium bromide 
• 36378-98-0 S-(dimethylamino)-S-phenyl(trans-2-phenyleth-1-enyl)oxosulfonium fluoroborate 
• 100-42-5 styrene 

Downstream Products

• 1264296-13-0 ethyl 2-benzylidene-5-(dimethylamino)-3-oxopent-4-enoate 
• 54023-37-9 ethyl 2-methyl-5-phenyl-4,5-dihydrofuran-3-carboxylate 
• 1263944-34-8 (1R,2S)-ethyl 2-phenyl-1-(3-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyrimidin-7-yl)cyclopropanecarboxylate 
• 1264297-02-0 (1S,2R)-ethyl 2-phenyl-1-(3-(4-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyrimidin-7-yl)cyclopropanecarboxylate 
• 1089672-14-9 ethyl 1-acetyl-2,4-diphenyl-2-(trimethylsilyloxy)cyclopentanecarboxylate 

Relevant academic research and scientific papers

Dimethyl-α-styrylsulphonium Bromide as a Reaction Intermediate

The addition product of styrene, bromine, and dimethyl sulphide was treated with bases to give the dimethyl-α-styrylsulphonium ion which reacted rapidly with various nucleophiles and also underwent slower base-catalysed rearrangement.

Organocatalytic Cloke-Wilson Rearrangement: DABCO-Catalyzed Ring Expansion of Cyclopropyl Ketones to 2,3-Dihydrofurans

An organocatalytic Cloke-Wilson rearrangement of cyclopropyl ketones to 2,3-dihydrofurans is exploited utilizing the homoconjugate addition process. With 1,4-diazabicyclo[2.2.2]octane as the catalyst, the rearrangement in DMSO at 120 °C proceeded in gener

S-Ethenylsulfoximine Derivatives. Reagents for Ethylenation of Protic Nucleophiles

The preparation of S-vinyl and S-(2-substituted)ethenyl derivatives of sulfoximines is described.Vinyl-, (2-phenylethenyl)-, (2,2-diphenylethenyl)-, (2-methyl-1-propenyl)-, (dimethylamino)phenyloxosulfonium fluoroborates were found to undergo an addition-elimination reaction sequence with protic nitrogen and carbon nucleophiles, resulting in ethylenation of the nucleophile and N,N-dimethylbenzenesulfinamide.Primary amines gave aziridines, enamines gave cyclopropyl derivatives of iminium salts or pyrrolidinium salts, anions of active methylene compounds gave dihydrofurans and/or cyclopropanes, and anions of nitroalkanes gave cyclic nitronic esters and/or nitrocyclopropanes.In several cases vinyl salts were generated in situ from β-methoxyoxosulfonium salts.Treatment of (-)-(S)-dimethylamino)phenyl(trans-2-phenylethenyl)oxosulfonium fluoroborate with methyl cyanoacetate in methanol containing sodium methoxide gave, in 81percent yield, (+)-(1S,2R)-methyl 1-cyano-2-phenylcyclopropanecarboxylate of 25.5percent optical purity.The same salt upon treatment with methyl nitroacetate gave, in 95percent yield, methyl 4-phenyl-3-isoxazolinecarboxylate 2-oxide with 33percent enantiomeric excess.Cyclopropanes were formed upon treatment of S-methyl-S-(trans-2-phenylethenyl)-N-(p-tolylsulfonyl)sulfoximine with anions of active methylene compounds.