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Acetylation of Ferrocene Gone Wrong?

I reacted my ferrocene product with acetic acid anhydride and phosphoric acid. Purified it via. flash chromatography and a dark red oil was produced.

I know that my product is not acetylferrocene as the NMR data looks as follows:

1H NMR
δH (300.1 MHz, CDCl3, Me4Si) 3.82, 2.62, 2.17, and 1.24.

13C{1H} NMR
211.0, 69.9, 69.5, 67.9, 53.7, 31.7 and 29.3.

Basically I am really confused as it no longer contains the aromatic regions seen in ferrocene/acetylferrocene at ~4.2 ppm. Any suggestions of what this product could be/what could have gone wrong e.g. moisture?

Thanks
Reply 1
Original post by Daviid02
I reacted my ferrocene product with acetic acid anhydride and phosphoric acid. Purified it via. flash chromatography and a dark red oil was produced.

I know that my product is not acetylferrocene as the NMR data looks as follows:

1H NMR
δH (300.1 MHz, CDCl3, Me4Si) 3.82, 2.62, 2.17, and 1.24.

13C{1H} NMR
211.0, 69.9, 69.5, 67.9, 53.7, 31.7 and 29.3.

Basically I am really confused as it no longer contains the aromatic regions seen in ferrocene/acetylferrocene at ~4.2 ppm. Any suggestions of what this product could be/what could have gone wrong e.g. moisture?

Thanks


Never done this before, but could it be doubly acetylated? but if like you said moisture has an effect, the ligand would simply fall off, right, thus won't leave you with the red oil, presumably still an organometallic complex?

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