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Organoiron complexes in organic synthesis : X. Nitromethylation and nucleophilic formylation of tricarbonylcyclohexadienyliumiron complexes by Anthony J. Pearson; Malcolm Chandler is a Chemistry article available to read on EtoBox.
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## Nitromethylation of the title complexes was found to be superior in some cases to the use of cyanide anion for regioselectivily introducing a C-N substituent on a cyclohesadiene ring. As a means of nucleophilic formylation the nitromethyl group was inferior to cyanide, the latter being reduced to aldehyde in moderate yield using diisobutylaluminium hydride. In connection with projects aimed at utilisation of diene-metal complexes in organic synthesis, we were interested in obtaining an efficient means of introducing a C-N group into tricarbonylcyclohexadieneiron complexes, and effecting carbonlrarbon bond formation which would complement the growing number of methods already available for this operation. Although cyanide anion has been used successfully for a number of cases [ 21, we have found in the present study that its reaction with the simple 2-methyl substituted compies (Ib) gives a 1 : 1 mixture of regioisomers (IIIb) and (VIIa) (see later), consistent with our earlier conclusion that regioselectivity of nucleophilic addition to this complex is determined mainly by steric, and not electronic factors [3], CN-being a sterically undemanding nucleophile. Furthermore, we have
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- Author
- Anthony J. Pearson; Malcolm Chandler
- Publisher
- Elsevier Science; Elsevier ; Elsevier BV (ISSN 0022-328X)
- Published
- 1980
- Language
- EN
- Field
- Chemistry (Physical Sciences)