I have done the experiment as the reference "Novel one-pot synthesis of 5-alkenyl-15-alkynylporphyrins and their derivatization to a butadiyne-linked benzoporphyrin dimer" provided, but I didn't succeed. Could you give me some advice?
Can you give us some additional information? For example, when you say that you didn't succeed, does that mean that you obtained none of the desired product? If so, how did you analyze for it? This preparation is a multi-step process: did you obtain reasonable yields of any of the intermediate products? What analytical techniques do you have to follow the courses of the various reactions?
Dear professor,
Thank you for your advice!
Actually I was hindered by the synthesis of bis(4,7-dihydro-4,7-ethano-2H-isoindol-1-yl) methane. Here is the process and the phenomena:
The raw material bis(3-ethoxycarbonyl-4,7-dihydro- 4,7-ethano-2H-isoindol-1-yl)methane was synthesized as the article suggested and the NMR of mine was the same as the reference. In the following step, when I monitored the reaction mixture by TLC plate with CH2Cl2 as eluent, no spot appeared (as showed in figure, the left plate). Afterwise, one spot was detected when CH2Cl2/ethyl acetate (1:1) was used (as showed in the figure, the right one). So I purfied the mixture by silica gel column chromatography with CH2Cl2/ethyl acetate (1:1). But the mixture seemed to be unstable on silica gel and several chrometapes changed from orange to red. I think the product was not the one I need or it was denatured. So could you give me some suggestions?
Sincerely,
Li Zeng
Mr./Miss/Mrs Zeng,
I do not know for exactly which conditions you are discussed and/or the content of paper 'one-pot synthesis....', but a fast search on the Reaxys database (https://www.reaxys.com/) showed that bis(4,7-dihydro-4,7-ethano-2H-isoindol-1-yl)methane can be obtained by the following scheme (attachment).
Usually their planes work, so that most probably you shall obtaine also your aimed product/intermediate easy as well.
The shown in the attachment references 1-4 are below:
1,2. Giraud-Roux, Maryline; Proni, Gloria; Nakanishi, Koji; Berova, Nina, Heterocycles, 2003 , vol. 61, p. 417 - 432
Syntheses and spectroscopic properties of methylbenzoate derivatives of tetrabenzoporphyrin, application to circular dichroism studies
3. Uno, Hidemitsu; Ito, Satoshi; Wada, Mitsuo; Watanabe, Hikaru; Nagai, Miho; Hayashi, Akiko; Murashima, Takashi; Ono, Noboru
Journal of the Chemical Society, Perkin Transactions 1, 2000 , # 24 p. 4347 - 4355,Synthesis and structures of pyrroles fused with rigid bicyclic ring systems at β-positions
4. Lucchi, Ottorino De; Lucchini, Vittorio; Pasquato, Lucia; Modena, Giorgio
Journal of Organic Chemistry, 1984 , vol. 49, # 4 p. 596 - 604, (Z)- and (E)-1,2-Bis(phenylsulfonyl)ethylenes as Synthetic Equivalents to Acetylene as Dienophile
If you discussed some of these papers and/or steps in them, than sorry for the 4r5epeating info.
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