27226-50-2Relevant articles and documents
Synthesis and reactivity of 2-thionoester pyrroles: A route to 2-formyl pyrroles
Kim, Min Joon,Gaube, Sophie M.,Beh, Michael H. R.,Smith, Craig D.,Thompson, Alison
, p. 31773 - 31780 (2019/10/19)
2-Functionalised pyrroles exhibit considerable synthetic utility. Herein, the synthesis and reactivity of 2-thionoester (-C(S)OR) pyrroles is reported. 2-Thionoester pyrroles were synthesised using a Knorr-type approach from aliphatic starting materials. 2-Thionoester pyrroles were reduced to the corresponding 2-formyl pyrroles, or the deuterated formyl variant, in one step using RANEY nickel, thereby removing the need for the much-utilised hydrolysis/decarboxylation/formylation steps that are typically required to convert Knorr-type 2-carboxylate pyrroles into 2-formyl pyrroles. 2-Thionoester pyrroles proved tolerant of typical functional group interconversions for which the parent 2-carboxylate pyrroles have become known.
Thermochemistry of substituted pyrroles
Berezin, M. V.,Semeikin, A. S.,V'yugin, A. I.,Krestov, G. A.
, p. 449 - 453 (2007/10/02)
The heats of solution of a series of substituted pyrroles in benzene, carbon tetrachloride, chloroform, DMF, and pyridine were measured by a calorimetric method at 298.15 K.The influence of substituents in the pyrrole molecule on the energy parameters of solvation by organic solvents is discussed.
The Chemistry of Pyrrolic Compounds. LXI Petroporphyrins from the Julia Creek Oil Shale: Further Evidence for the Derivation of Aetiotype Petroporphyrins from Chlorophyll
Clezy, Peter S.,Fookes, Christopher J. R.,Prashar, Jognandan K.
, p. 775 - 786 (2007/10/02)
The synthesis of the porphyrins (2c-j) has been achieved by the oxidative cyclization of appropriately substituted biladienes-ac.The availability of authentic material has allowed the finalization of the structure of a series of aetiotype fossil porphyrins which vary in substitution pattern at positions 3 and 13.All combinations of H, Me and Et at these positions have now been isolated from natural sources.This points to a common precursor, possibly a divinylporphyrin, and strengthens the belief that the chlorophylls are the prime source of the petroporphyrins.A vinyl group, or a close derivative, is found at position 3 of all chlorophylls while fragmentation of the ubiquitous isocyclic ring of the chlorophylls could yield the vinyl group at position 13.
