136290-37-4

Upstream product

• 288-88-0 1,2,4-Triazole 
• 14371-10-9 (E)-3-phenylpropenal 
• 122-51-0 orthoformic acid triethyl ester 

Downstream Products

• 183679-01-8 ((Z)-4-Ethoxy-1,2-diphenyl-4-[1,2,4]triazol-1-yl-but-3-enyl)-phenyl-amine 
• 69573-50-8 4-spirocyclohexane-3-phenyl-γ-butyrolactone 
• 57697-68-4 4,5,5-triphenyldihydrofuran-2(3H)-one 
• 72277-18-0 ethyl 3,4-diphenylbutanoate 
• 67478-54-0 ethyl 3-ethyl-3-phenylpropionate 
• 20453-83-2 4,5-diphenyldihydrofuran-2(3H)-one 
• 13133-96-5 4-hydroxy-4-methyl-3-phenylpentanoic acid γ-lactone 
• 1026409-03-9 1-((Z)-1-Ethoxy-3,4-diphenyl-but-1-enyl)-1H-[1,2,4]triazole 

Relevant academic research and scientific papers

Benzotriazole- and 1,2,4-triazole-stabilized allylic anions: Applications in syntheses of functionalized α,β-unsaturated ketones, γ-lactones, γ-lactams, and β-substituted esters

Deprotonated 1-(benzotriazol-1-yl)-1-ethoxy-2-hexene (7) reacted with alkyl halides, aldehydes, ketones, imines, and α,β-unsaturated esters to give exclusively the α-alkylated products 8a-c, 10a,b, 12, 14, 16, and 18a,b, respectively. Without isolation, these products were hydrolyzed under mild conditions to generate the corresponding simple or functionalized α,β-unsaturated ketenes 9a-c, 11a,b, 13, 15, 17, and 19a,b. Similar reactions with the phenyl-substituted analog 3-(benzotriazol-1-yl)-3-ethoxy-1-phenyl-1-propene (21) also gave the analogous α-products, but they were accompanied by small amounts of the γ-products in most cases. By contrast, deprotonation of the corresponding triazole derivative 29 with butyllithium followed by reactions with alkyl halides, aldehydes, ketones, or imines yielded exclusively γ-alkylated adducts 32, 34, 36, 38, 40, and 42. Intermediates 32, 34, 36, 38, 40, and 42 were readily converted into β-substituted esters 33a-c, γ-lactones 35a,b, 39, 41, and 43, and γ-lactams 37a-c on hydrolysis.