4391-87-1Relevant academic research and scientific papers
An inexpensive, selective procedure for oxidizing α-methyl to α-formyl pyrroles
Bobál,Lightner
, p. 1219 - 1221 (2001)
α-Methylpyrroles are converted to α-formyl by sodium bromate in aqueous methanol in ～60% yield. Adding 1% ceric ammonium nitrate as a co-oxidant brings the isolated yields of synthetically useful 2-formylpyrroles 2a-d up to ～70%, or close to those found when using only the considerably more expensive ceric ammonium nitrate as oxidant.
Dipyrrinone imines: Controlling self-association
Ward, Patrick,Chandler, Rebecca R.,Huggins, Michael T.
, p. 286 - 291 (2013)
We report the synthesis of three new dipyrrinone imine analogues and the characterisation of their self-association properties. Based on vapour pressure osmometry and nuclear magnetic resonance studies, placing the imine functional group at C(9) of the di
Stable 4E-dipyrrinones
Boiadjiev, Stefan E.,Lightner, David A.
, p. 10871 - 10886 (1999)
Dipyrrinones formed by DBU and n-Bu3P-promoted condensation of 5-p- toluenesulfonylpyrrolinones with pyrrole 2-aldehydes, gave high yields of product with predominantly the E-configuration when the aldehyde had a 5- carboethoxy group. The 4E-dipyrrinones were readily purified by chromatography and were stable in solutions shielded from light.
Electrophilic Heteroaromatic Reactions. 3. The α-Side-Chain Bromination of Some Polysubstituted α-Methylpyrroles in the Dark. Evidence for the Formation of Intermediate ? Adducts
Angelini, Giancarlo,Giancaspro, Carlo,Illuminati, Gabriello,Sleiter, Giancarlo
, p. 1786 - 1790 (1980)
The bromination of some ethyl 3,5-dimethyl-4-R-pyrrole-2-carboxylates (R = alkyl, Br, Cl, CO2Et) with molecular bromine in dichloroethane solution, in the dark, occurs smoothly at room temperature to yield the corresponding 5-bromomethyl derivatives.The course of the reaction was followed by titrimetric, spectrophotometric, and NMR methods.The reaction can be regarded as an extreme case of behavior in the interaction of aromatic systems with electrophiles, as it consists of two separately observable processes.Upon addition of bromine to the solution of the pyrrole, a number of cationic ? adducts form as a result of attack on all carbon positions of the pyrrole ring to varying extents.The adducts then decompose relatively slowly to a single substitution product.Each of the 4-R groups appears to affect the rates of the two main steps in opposite ways.This is interpreted in terms of stabilization of the reaction intermediate.
A new convergent method for porphyrin synthesis based on a '3 + 1' condensation
Boudif, Arezki,Momenteau, Michel
, p. 1235 - 1242 (2007/10/03)
A new methodology based on the '3 + 1' acid-catalytic condensation of tripyrranes and pyrrole-2,5-dicarbaldehyde has been used, for the first time, for the synthesis of two types of porphyrins: vic-dipropionic ester porphyrins 30 and 31 including an analo
Oxidation of pyrrole α-methyl to formyl with ceric ammonium nitrate
Thyrann, Thomas,Lightner, David A.
, p. 4345 - 4348 (2007/10/02)
Pyrrole α-aldehydes can be prepared in high yield by oxidation of pyrrole α-methyl groups with ceric ammonium nitrate when the pyrrole ring also has an α-carboxylic acid ester group.
