Electron-transfer Rearrangements of Dibenzodiazocine Derivatives: Effective Electron Traps for Organometallic Reactions
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1 The John Eisch Organometallic Symposium Binghamton University, NY Electron-transfer Rearrangements of Dibenzodiazocine Derivatives: Effective Electron Traps for Organometallic Reactions Renuka Manchanayakage October 29, 2011
2 Postdoctoral Work at Eisch Group Synthesis and study of iron carbene complexes as potential polymerization and olefin metathesis catalysts. Study electron-transfer rearrangements of diazocine derivatives. Eisch, John; Manchanayakage, Renuka; Rheingold, Arnold.* Org. Lett., 2009, 11, Eisch, John; Yu, Kun; Rheingold, Arnold.* Research in Progress. * X-ray studies at Department of Chemistry and Biochemistry, University of California, San Diego
3 Dibenzodiazocine Derivatives Structural configuration: Tub-like nonplanar eightmembered rings (Heterocyclic model for cyclooctatetraene).
4 Reduction of Dibenzodiazocines Can they form planar dianion upon addition of two electrons???
5 Previous Studies: Reduction with Na(Hg) in EtOH The structure of the product was established by elemental analysis and IR spectroscopy. Allinger, N.; Youngdale, G. J. Org. Chem. 1958, 24, 306
6 Previous Studies: LiAlH 4 Reduction The structure of the product was established by elemental analysis, IR spectroscopy and chemical analysis.
7 Previous Studies: Proposed Mechanism for LiAlH 4 Reduction Initiated by the attack of hydride at one of the azomethine carbons. Nucleophilic attack by the amide ion on the phenyl ring. Allinger, N.; Youngdale, G. J. Org. Chem. 1958, 24, 306
8 Na/THF Reduction of [1,4]Diazocine Derivative The crude product confirmed the presence of benzophenyl ketone and carbazol as byproducts. Byproducts were separated by flash column chromatography. The product was recrystallized by hot 95% ethanol. Eisch, J.; Manchanayakage, R.; Rheingold, A. Org. Lett., 2009, 11, 4060
9 Spectroscopic and Chemical Confirmation of the Product NMR spectroscopy and mass spectrometry data were collected. IR data confirmed the presence of primary amine group. Chemical confirmation by refluxing with acetic acid in aqueous HCl to form a known ketone.
10 X-ray and Melting Point Analysis of the Product E-isomer: Triclinic, colorless needles mp = C Z-isomer: Orthorhombic, pale yellow block-type crystals mp = C
11 Proposed Mechanism for the Na/THF Reduction Intramolecular coupling of N- and C-centered radicals in the non-planar bis-radical anion. Eisch, J.; Manchanayakage, R.; Rheingold, A. Org. Lett., 2009, 11, 4060
12 Validation of the Proposed Mechanism Other examples for intramolecular formation and coupling of bis-radical anions by alkali metals. Eisch et al. 1988, Rickhaus et al. 2010
13 Why This Pathway? Attaining the planarity for Hückel aromaticity faces two energy barriers. 1. Minimum repulsion energy of ortho H atoms of planar intermediate is 20 kcal/mol. 2. The ring strain energy of producing an allplanar eight-membered ring is assessed at about 23 kcal/mole more.
14 Electron-transfer Rearrangements of 6,12- diphenyldibenzo[b,f][1,5]diazocine Nonplanar, tub-like structure The coplanarity of the transannular C=N and N=C groups with the crossring N1 and N2 atom separations of Å and the C25 - C26 atom separation of o A.
15 Na/THF Reduction of [1,5]Diazocine Derivative Eisch, J.; Yu, K.; Rheingold, A. Research in Progress
16 SET Reductions of Diazocines with Various Organometallics SET reduction Adduct
17 SET Reductions with Benzylic Lithium Reagents (Path A)
18 SET Reductions with Organomagnesium Reagents (Path B) Reaction with allylmagnesium chloride afforded the hydrolysis adduct at room temperature. Heating and illumination of the reaction showed the formation of diimide through transannular electron delocalization.
19 Conclusions and Future Remarks Dibenzodiazocines can undergo profound rearrangements upon electron-transfer reductions. These compounds possess enhanced electron capture properties. The most effective electron trap for the detection of electron transfer in organometallic reactions with organic substrates. Study of SET reactions under thermal or photochemical conditions. Investigation of intermediates formed during transannular electron delocalization, using EPR method.
20 Acknowledgement Prof. John Eisch Organization Committee, Eisch Organometallic Symposium Prof. Arnold Reingold X-ray studies Prof. David Doetschman EPR studies Kun Yu Chemistry Department Susquehanna University The John Eisch Organometallic Symposium Binghamton University, NY
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