50488-52-3

Upstream product

• 3577-87-5 diphenyl methyl phosphite 
• 590-17-0 cyanomethyl bromide 
• 108-95-2 phenol 
• 2524-64-3 chlorophosphoric acid diphenyl ester 
• 75-05-8 acetonitrile 

Downstream Products

• 5320-30-9 trans-5-phenylpent-2-enenitrile 
• 82125-05-1 (Z)-5-phenyl-2-pentenonitrile 
• 1885-38-7 cinnamic nitrile 
• 24840-05-9 (Z)-cinnamonitrile 
• 1418755-33-5 diphenyl [cyano(diazo)methyl]phosphonate 
• 22031-57-8 (E)-3-cyclohexylprop-2-enenitrile 
• 78978-70-8 (Z)-3-cyclohexylprop-2-enenitrile 
• 1026935-65-8 (2E,4E)-3-Methyl-5-(2,6,6-trimethyl-3-triethylsilanyloxy-cyclohex-1-enyl)-penta-2,4-dienenitrile 

Relevant academic research and scientific papers

Highly Z-selective synthesis of a,b-unsaturated nitriles using the Horner-Wadsworth-Emmons reaction

A new HWE reagent, (o-tBuC6H4O)2P(O)CH2CN (2e), reacts with various types of aldehydes to give Z-a,bunsaturated nitriles with 86% to >99% Z-selectivity. Especially, the reaction of 2e with bulkier aldehydes, both aromatic and aliphatic, gave the Z-olefins with extremely high selectivity. The combination of t-BuOK and 18-crown-6 (1 equiv) is the base of choice for aromatic aldehydes and t-BuOK is generally the base of choice for aliphatic aldehydes.

An efficient and practical synthesis of diphenyl cyanomethylenephosphonate: Applications to the stereoselective synthesis of cis-α,β-unsaturated nitriles

Diphenyl cyanomethylenephosphonate (PhO)2POCH2CN was prepared as a stable crystalline solid in high yield in a single step from acetonitrile, LDA, and (PhO)2P(O)CI. The potassium ylide generated from this compound afforded α,β-unsaturated nitriles upon reacting with aldehydes, with a stereoselectivity of 64-100% favoring the cis-isomer.