Further Studies on Steric Deformation<sup>1</sup>

Ellingson, Rudolph C.; Corwin, Alsoph H.

doi:10.1021/ja01210a061

Cited by 15 publications

(4 citation statements)

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“…Dimethyl sulphate appeared to be ineffective as a methylating agent, as McEwen had found in his early experiments,' and we turned to the use of the recently discovered and highly potent alkylating reagent, methyl fl~orosulphonate.~~ Most of our experiments with this reagent were carried out with octaethylporphyrin in hot o-dichlorobenzene and, in addition to the N-methyl (FIGURE 2) (7) and tram N,Ncdimethyl- (8) porphyrins, two other red N,N'-dimethyl porphyrins, and a bright green N,N',N"-trimethylporphyrin were also formed.14 These were separated by a combination of chromatographic and counter-current distribution procedures and shown by spectral analyses to be the cis-and trans-N.N,-dimethyloctaethylporphyrins (9) and (10) and truns-truns-N.NbN,-trimethyloctaethyIporphyrin salt (11).…”

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confidence: 99%

N‐methylporphyrins

Jackson

Dearden

1973

Annals of the New York Academy of Sciences

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confidence: 99%

N‐methylporphyrins

Jackson

Dearden

1973

Annals of the New York Academy of Sciences

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“…The chemistry of N-methylated porphyrins has been investigated over many years although interest has been mainly in the noncarboxylated synthetic porphyrins. [14][15][16][17][18] The N-methylated, N-ethylated and N-1 -propylated mesoporphyrin IX dimethyl esters reported here were prepared for comparison with the pigment produced in the liver of mice after the administration of 3,5-diethoxycarbonyl-1,4-dihy-dr~collidine.~ Monoalkylations proceeded with few side products and gave good yields except for N-1 -propylated mesoporphyrin and coproporphyrin which -were formed in yields of 5-10 YO. Previously N-propylations of porphyrins with l-iodopropane could not be achieved.I6 During TLC two tailing bands were consistently observed.…”

Section: Resultsmentioning

confidence: 99%

Dealkylation during electron impact mass spectrometric analysis ofN- monoalkylated porphyrin methyl esters

Smith

Farmer

1982

Biol. Mass Spectrom.

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The N-monomethylated, N-monoethylated and N-mono-1-propylated homologues of mesoporphyrin IX dimethyl ester and the corresponding methylated and 1-pr6pylated homologues of coproporphyrin 111 tetramethyl ester have been prepared. Substituted porphyrins in a series could be distinguished from each other and from the parent porphyrin by their dication absorption spectra. All compounds gave molecular ions of varying intensities during electron impact mass spectrometry but thermal Ndealkylation to mesoporphyrin IX or coproporphyrin 111 methyl esters occurred readily and it was difficult to obtain spectra not showing fragmentation ions derived from this process. The compounds serve as models for the 'green pigments' produced in oioo by the action of some drugs and illustrate the problem of dealkylation during their analysis by electron impact mass spectrometry.

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“…(1) pyrrole ring I (Fig. 1) being somewhat out of the over-all plane of the ring with its nitrogen above the plane and its 0-carbons below; (2) rings II and IV being out of the plane, to a lesser extent, with their nitrogen atoms below and their 0-carbons above; and (3) ring III remaining essentially in the plane. The n.m.r.…”

Section: -189°decmentioning

confidence: 99%