1219505-45-9

Basic information

• Product Name: Br^(1-)*C₁₈H₂₅N₂O₃⁽¹⁺⁾
• CAS NO: 1219505-45-9
• Molecular Weight: 397.312
• Mol File: 1219505-45-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Br^(1-)*C₁₈H₂₅N₂O₃⁽¹⁺⁾(CAS DataBase Reference)
• NIST Chemistry Reference: Br^(1-)*C₁₈H₂₅N₂O₃⁽¹⁺⁾(1219505-45-9)
• EPA Substance Registry System: Br^(1-)*C₁₈H₂₅N₂O₃⁽¹⁺⁾(1219505-45-9)

Safety Data

• Hazardous Substances Data: 1219505-45-9(Hazardous Substances Data)

Upstream product

• 280-57-9 1,4-diaza-bicyclo[2.2.2]octane 
• 213999-88-3 methyl (2Z)-2-(bromomethyl)-3-(4-methoxyphenyl)prop-2-enoate 

Relevant articles and documents

SN2' versus SN2 reactivity: Control of regioselectivity in conversions of Baylis-Hillman adducts

TiCl4-induced Baylis-Hillman reactions of α,β- unsaturated carbonyl compounds with aldehydes yield the (Z)-2-(chloromethyl) vinyl carbonyl compounds 5, which react with 1,4diazabicyclo[2.2.2]octane (DABCO), quinuclidine, and pyridines to give the allylammonium ions 6. Their combination with less than one equivalent of the potassium salts of stabilized carbanions (e.g. malonate) yields methylene derivatives 8 under kinetically controlled conditions (SN2' reactions). When more than one equivalent of the carbanions is used, a second SN2' reaction converts 8 into their thermodynamically more stable allyl isomers 9. The second-order rate constants for the reactions of 6 with carbanions have been determined photometrically inDMSO. With these rate constants and the previously reported nucleophilespecific parameters N and s for the stabilized carbanions, the correlation log k (20°C) = s(N + E) allowed us to calculate the electrophilicity parameters E for the allylammonium ions 6 (-19 a rate-determining addition step.