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A synthetic approach of new trans-substituted hydroxylporphyrins.

Daphnomili D, Grammatikopoulou M, Raptopoulou C, Charalambidis G, Lazarides T, Coutsolelos AG - Bioinorg Chem Appl (2010)

Bottom Line: All of the synthesized products were characterized by (1)H-N.M.R., (13)C-N.M.R., and H.R.M.S.Electrochemical studies revealed two one-electron oxidations and two reductions.In addition, the X-ray structure of one methoxy-derivative was determined.

View Article: PubMed Central - PubMed

Affiliation: Laboratory of Bioinorganic Coordination Chemistry, Department of Chemistry, School of Sciences, University of Crete, P.O. Box 2208, Heraklion 71003, Crete, Greece.

ABSTRACT
The synthesis of new trans A(2)B(2)-substituted porphyrins bearing oxygenic substituent (methoxy, acetoxy, hydroxy) at the periphery of the ring are described. All of the synthesized products were characterized by (1)H-N.M.R., (13)C-N.M.R., and H.R.M.S. Electrochemical studies revealed two one-electron oxidations and two reductions. In addition, the X-ray structure of one methoxy-derivative was determined.

No MeSH data available.


6αα and 6αβ atropoisomers.
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sch2: 6αα and 6αβ atropoisomers.

Mentions: Compound 2 is a mixture of atropisomers that proved to be inseparable despite our repeated efforts for chromatographic separation. Compounds 5 and 6 were obtained by cleavage of the methyl ether by BBr3 (Scheme 1), while 7 is obtained by alkaline hydrolysis of the ester group or alternative by cleavage of the methoxy group. The two isomers of compound 6 (Scheme 2) in contrast to these of 2 are easily separated by silica gel chromatography. 6αβ is eluted with CH2Cl2/Hexane (6/4 v/v) while the more polar 6αα is eluted with 0.5% EtOH /CH2Cl2.


A synthetic approach of new trans-substituted hydroxylporphyrins.

Daphnomili D, Grammatikopoulou M, Raptopoulou C, Charalambidis G, Lazarides T, Coutsolelos AG - Bioinorg Chem Appl (2010)

6αα and 6αβ atropoisomers.
© Copyright Policy - open-access
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC2901623&req=5

sch2: 6αα and 6αβ atropoisomers.
Mentions: Compound 2 is a mixture of atropisomers that proved to be inseparable despite our repeated efforts for chromatographic separation. Compounds 5 and 6 were obtained by cleavage of the methyl ether by BBr3 (Scheme 1), while 7 is obtained by alkaline hydrolysis of the ester group or alternative by cleavage of the methoxy group. The two isomers of compound 6 (Scheme 2) in contrast to these of 2 are easily separated by silica gel chromatography. 6αβ is eluted with CH2Cl2/Hexane (6/4 v/v) while the more polar 6αα is eluted with 0.5% EtOH /CH2Cl2.

Bottom Line: All of the synthesized products were characterized by (1)H-N.M.R., (13)C-N.M.R., and H.R.M.S.Electrochemical studies revealed two one-electron oxidations and two reductions.In addition, the X-ray structure of one methoxy-derivative was determined.

View Article: PubMed Central - PubMed

Affiliation: Laboratory of Bioinorganic Coordination Chemistry, Department of Chemistry, School of Sciences, University of Crete, P.O. Box 2208, Heraklion 71003, Crete, Greece.

ABSTRACT
The synthesis of new trans A(2)B(2)-substituted porphyrins bearing oxygenic substituent (methoxy, acetoxy, hydroxy) at the periphery of the ring are described. All of the synthesized products were characterized by (1)H-N.M.R., (13)C-N.M.R., and H.R.M.S. Electrochemical studies revealed two one-electron oxidations and two reductions. In addition, the X-ray structure of one methoxy-derivative was determined.

No MeSH data available.