10409-55-9

Upstream product

• 999-01-9 O,O'-diethyl thiophosphonate 
• 7473-99-6 α-chloroisobutyrophenone 
• 762-04-9 phosphonic acid diethyl ester 
• 122-52-1 triethyl phosphite 
• 814-49-3 diethyl chlorophosphate 
• 611-70-1 phenyl isopropyl ketone 
• 10409-54-8 2-bromo-2-methyl-1-phenyl-propan-1-one 

Downstream Products

• 14161-67-2 1-methyl-4-(2-methyl-1-phenylprop-1-en-1-yl)benzene 

Relevant academic research and scientific papers

Aluminum Chloride Promoted Cross-Coupling of Trisubstituted Enol Phosphates with Organozinc Reagents En Route to the Stereoselective Synthesis of Tamoxifen and Its Analogues

A new method for the stereoselective cross-coupling reaction of arylzinc chlorides with trisubstituted enol phosphates is described. The developed method requires aluminum chloride as a promoter, and the reaction conditions tolerate various functional groups. The observed reactivity pattern of trisubstituted enol phosphates was used for the stereoselective preparation of tamoxifen and its analogues.

Reaction ofα- Halo Ketones with Nucleophiles

p-Nitro- or p-cyanophenacyl chloride or the 1,1-dimethyl derivatives react with the anion of 2-nitropropane to form the C-alkilation product by a radical chain mechanism (SRN1).With the 1,1-dimethyl derivatives, the free radical substitution is photostimulated and occurs in competition with ionic reactions leading to the oxiranes 5 and hydroxy ketones 6.When K+ is used as the counterion, the SRN1 process is favored by complexation with 18-crown-6. p-Nitro-1,1-dimethylphenacyl chloride gives substitution products with diethyl malonate or diethyl mthylmalonate anions via the SRN1 process, but with PhS- or p-MeC6H4SO2-, substitution occurs by competing ionic and radical processes.Propylacetylenide anion reacts to form the oxirane 13a while diethyl phosphite or thiophosphite anions yield the enol phosphate 14a or thiophosphate 14b. 1,1-Dimethylphenacyl chloride reacts by nonradical processes to give the oxirane with acetylenide anions, the substitution products with PhS- or p-MeC6H4SO2- and a mixture of the enol phosphate, and oxirane 16 with diethyl phosphite anion.With Me2C==NO2-K+, mainly the oxirane is formed in Me2SO but mainly substitution via the SRN1 chain is observed in HMPA.