58177-60-9

Upstream product

• 83-38-5 2,6-dichlorobenzaldehyde 
• 75-05-8 acetonitrile 
• 142846-49-9 N-[1-(2,6-Dichloro-phenyl)-meth-(Z)-ylidene]-4-methyl-benzenesulfonamide 
• 16640-68-9 cyanomethylene triphenylphosphorane 
• 433231-64-2 C₂₀H₁₀F₁₂NO₂P 

Relevant academic research and scientific papers

Stereoselective olefination of N-sulfonyl imines with stabilized phosphonium ylides for the synthesis of electron-deficient alkenes

An unprecedented protocol has been developed for thestereoselective synthesis of structurally diverse electron-deficient alkenes in moderate to excellent yields from readily accessible N-sulfonyl imines and stabilized phosphonium ylides. Significantly, the olefination reaction of N-sulfonylimines with nitrile-stabilized phosphonium ylides affords an array of α,β-unsaturated nitriles with high Z selectivity, and the reactions with ester-, amide-, and ketone-stabilized phosphonium ylides afford α,β-unsaturated esters, amides, and ketones with high E selectivity, respectively. Spectroscopic analysis of the reaction mixtures and trapping of the intermediates allow plausible mechanisms to be proposed. Initialimine/ylide addition leads to the formation of betaines that cyclize to form 1,2-azaphosphetanes that subsequently eliminate iminophosphoranes to yield alkenes. For the synthesis of electron-deficient 1,2-disubstituted alkenes, the presence of an electron-withdrawing group in the betaine allows rapid interconversion between its two diastereomers through proton transfer. The Z/E selectivity for alkene synthesis is determined by the different rates at which the two betaine diastereomers form the corresponding 1,2-azaphosphetane diastereomers. In contrast, the Z/E selectivity for the synthesis of electron-deficient trisubstituted alkenes originates from the diastereoselective addition of stabilized phosphonium ylides to N-sulfonyl imines.

Transition metal-catalyzed synthesis of pyrroles from dienyl azides

(Chemical Equation Presented) A range of 2,5-disubstituted and 2,4,5-trisubstituted pyrroles can be synthesized from dienyl azides at room temperature using catalytic amounts of Znl2 or Rh2(O 2CC3F7)4.

Highly Z-selective synthesis of disubstituted α, β-unsaturated cyanides and amides using 10-P-5 wittig type reagents

Phosphoranes (10-P-5) bearing cyanomethyl, acetamide, and N, N-dimethylacetamide groups were examined for Wittig type reactions. All three reacted to give the corresponding olefins. The reaction of the cyanomethyl reagent with aldehydes gave α, β-unsatura