Highly nucleophilic triphenylphosphines.

Synthesis of highly substituted pyrroles via nucleophilic catalysis.

A nucleophilic catalysis method providing a concise synthesis of di-, tri-, and tetrasubstituted pyrroles is described. This regioselective one-pot method relies on nucleophilic catalysis of the intermolecular addition of oximes to activated alkynes and thermal rearrangement of the in situ generated O-vinyl oximes to form pyrroles that contain a functional group handle at the C3/C4 position.

Highly Efficient Intramolecular Nucleophilic Reactions. The Cyclization of p-Nitrophenyl

p-Nitrophenyl N-(2-mercaptophenyl)-N-methylcarbamate cyclizes rapidly at 25' to N-methylbenzothiazolone with release of p-nitrophenol. The pH-rate constant profile is sigmoidal with pK,,, = 8.7. The effective molarity of the neighboring sulfhydryl group is 1.4 X los M in comparison with bimolecular attack of thiols on p-nitrophenyl N-methyl-Nphenylcarbamate. The pH-rate constant profile for cyc...

Highly nucleophilic dipropanolamine chelated boron reagents for aryl-transmetallation to iron complexes.

New aryl- and heteroarylboronate esters chelated by dipropanolamine are synthesised directly from boronic acids. The corresponding anionic borates are readily accessible by deprotonation and demonstrate an increase in hydrocarbyl nucleophilicity in comparison to other common borates. The new borates proved competent for magnesium or zinc additive-free, direct boron-to-iron hydrocarbyl transmeta...

Nucleophilic Substitution and Elimination

What does the term "nucleophilic substitution" imply? • A nucleophile is an the electron rich species that will react with an electron poor species • A substitution implies that one group replaces another. Nucleophilic substitution reactions occur when an electron rich species, the nucleophile, reacts at an electrophilic saturated C atom attached to an electronegative group (important), the lea...

Modern Nucleophilic Aromatic Substitution