90289-81-9

Upstream product

• 118653-24-0 methyl(E)-N-formyl-N-(2-phenylethenyl)acetamide 
• 84353-56-0 (E)-N-(2-phenylethenyl)-2,2,2-trifluoroacetamide 
• 2258-42-6 formyl acetic anhydride 
• 33066-20-5 (E)-1-isocyanato-2-phenylethene 
• 73885-72-0 trans-N-methoxycarbonyl-2-phenylethenylamine 
• 1722-84-5 (E)-N-styrylacetamide 
• 109053-92-1 N-(2-Phenyl-1-trimethylsilanyloxy-ethyl)-formamide 
• 153469-65-9 ((E)-Styryl)-selenocarbamic acid Se-phenyl ester 

Downstream Products

• 41003-97-8 (E)-2-Phenylvinyl Isocyanide 

Relevant academic research and scientific papers

Reactions of 1-acylamino-1-(trimethylsiloxy)alkanes: Versatile precursors to acylimines

1-Acylamino-1-(trimethylsiloxy)alkanes react with carbon and heteroatom nucleophiles to give the corresponding 1-substituted-1-acylaminoalkanes. The 1-acylamino-1-(trimethylsiloxy)alkanes can also give rise to enamides, and by this route the mild antibiotic tuberin, and the isomeric (Z)-tuberin have been prepared. A further example of their reactions is illustrated with the acid-catalysed intramolecular cyclisation onto a carbon-carbon double bond. These transformations show that 1-acylamino-1-(trimethylsiloxy)alkanes are versatile precursors to synthetically useful acylimines.

Synthesis and reactions of N,N-bis[1-(trimethylsiloxy)alkyl]-formamides: Preparation of (±)-argemonine and (±)-norargemonine

Symmetrical and unsymmetrical N,N-bis[1-(trimethylsiloxy)alkyl]formamides are prepared and their reactions investigated, including an application to the synthesis of the pavine alkaloids (±)-argemonine and (±)-norargemonine.

The Conversion of Carboxylic Acids into Isonitriles via Selenium-Phenyl Selenocarbamates

Carboxylic acids are converted into isonitriles via Schmidt rearrangement of the derived acyl azides, addition of phenylselenol to the resultant isocyanate, tributylstannane reduction and dehydration.

Synthesis of Enamides

(Z)-3-Arylprop-2-enoic acids can be converted by the Curtius procedure, through the acyl azides, into (Z)-2-arylethenyl isocyanates, which with methanol give methyl (Z)-N-(2-arylethenyl)carbamates.Acylation of the (Z)-enecarbamates, through their anions, leads to methyl (Z)-N-acyl-N-(2-arylethenyl)carbamates, which on treatment with lithium iodide in boiling N,N-dimethylformamide or acetonitrile undergo demethoxycarbonylation to give (Z)-enamides.The stereospecific route to enamides can also be used in the E-series.Treatment of (Z)- or (E)-2-arylethenyl isocyanates with trifluoroacetic acid gives (E)-N-(2-arylethenyl)trifluoroacetamides,the anions of which, with acylating agents, give (E)-enamides directly.