74591-98-3

Upstream product

• 603-35-0 triphenylphosphine 
• 5460-29-7 2-(3-bromopropyl)isoindole-1,3-dione 
• 99-61-6 3-nitro-benzaldehyde 
• 7743-29-5 [3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propyl]-triphenyl-phosphonium bromide 
• 84812-12-4 (2,6-dimethoxyphenyl)diphenyl(3-phthalimidopropyl)phosphonium bromide 

Downstream Products

• 84812-15-7 (E)-2-(4-(3-nitrophenyl)but-3-en-1-yl)isoindoline-1,3-dione 
• 74592-03-3 (Z)-4-(3-Nitro-phenyl)-but-3-enylamine; hydrochloride 

Relevant academic research and scientific papers

Role of the Through-Space 2p-3d Overlap Effect in the Wittig Reaction

Reactions of the ylide derived from triphenyl(3-phthalimidopropyl)phosphonium bromide with aromatic aldehydes have been reported to give exclusively the Z alkenes.On the basis of the Bestmann mechanism for the Wittig reaction, and also because of the fact that a 2,6-dimethoxyphenyl group enters into a strong through-space 2p-3d overlap interaction with an adjacent phosphonio group, we postulated that the reactions of the ylide derived from (2,6-dimethoxyphenyl)diphenyl(3-phthalimidopropyl)phosphonium bromide with aromatic aldehydes would give substantial ratios of E:Z alkenes.This proved to be the case.