Romano Andruzzi

Bio: Romano Andruzzi is an academic researcher from University of Minnesota. The author has contributed to research in topics: Cyclic voltammetry & Polarography. The author has an hindex of 11, co-authored 28 publications receiving 254 citations.

Radical cations. Part 2. Oxidative dimerization of indolizines: a chemical and electrochemical investigation

Abstract: 3-Unsubstituted indolizines undergo oxidative dimerization in the presence of catalytic amounts of FeIII and oxygen. Although much experimental evidence apparently indicates that FeII is reoxidised to FeIII by oxygen, a chain mechanism cannot be envisaged. A chain sequence can be proposed only in the case where a stoicheiometric amount of FeIII is used.

Selective cathodic Birch reductions

Abstract: Etude de la reduction de l'anisole, (methoxy-6 tetrahydro-1,2,3,4) naphtalene, hexyne-1, methoxy-3β œstratriene-1,3,5(10)one-17 et methoxy-3β nor-19 pregnenyne-20ol-1

Electrografting: a powerful method for surface modification

Abstract: Electrografting refers to the electrochemical reaction that permits organic layers to be attached to solid conducting substrates. This definition can be extended to reactions involving an electron transfer between the substrate to be modified and the reagent, but also to examples where a reducing or oxidizing reagent is added to produce the reactive species. These methods are interesting as they provide a real bond between the surface and the organic layer. Electrografting applies to a variety of substrates including carbon, metals and their oxides, but also dielectrics such as polymers. Since the 1980s several methods have been developed, either by reduction or oxidation, and some of them have reached an industrial stage. This critical review describes the methods that are used for electrografting, their mechanism, the formation and growth of the layers as well as their applications (742 references).

Total synthesis of dixiamycin B by electrochemical oxidation.

Abstract: N–N-linked dimeric indole alkaloids represent an unexplored class of natural products for which chemical synthesis has no practical solution. To meet this challenge, an electrochemical oxidative dimerization method was developed, which was applied as the pivotal step of the first total synthesis of dixiamycin B. This method is also general for N–N dimerization of substituted carbazoles and β-carbolines, providing entry into seldom explored chemical space.

Synthesis, cyclic voltammetric studies, and electrogenerated chemiluminescence of a new phenylquinoline-biphenothiazine donor-acceptor molecule.

Abstract: We report the synthesis, electrochemistry, and luminescence of a novel ECL emitting compound containing two electron-accepting hexyl-phenylquinoline groups covalently attached to the 3,3‘-positions of the electron-donating 10,10‘-dimethylbiphenothiazine group. The optimized geometry as determined from semiempirical MNDO calculations shows that the two quinoline groups are twisted 82.5° from the two phenothiazine rings, indicating a lack of electron delocalization among these groups. This unique geometry allows generation of localized radical cations and radical anions capable of generating ECL upon annihilation. However, the phenothiazine rings are twisted 46.5° relative to each other, suggesting possible interactions between the two moieties. This is evident in the electrochemical behavior in which two closely spaced one-electron oxidations, rather than a single two-electron oxidation wave, were observed. The photophysical properties of BHQ-BPZ show strong resemblances to the parent compound, BPQ-PTZ, wh...

Total synthesis of (+/-)-psychotrimine.

Abstract: A new process for the union of anilines with tryptamine derivatives has been developed, furnishing C-3 quaternized pyrroloindoline architectures. This chemoselective coupling of a tryptamine with 1.2 equiv of 2-iodoaniline proceeds efficiently on a gram-scale using only the simple reagents N-iodosuccinimide and triethylamine. Using this new reaction, the complex natural product psychotrimine has been fashioned with a rare level of efficiency and practicality. From a readily available bromotryptamine, only four steps (41−45% overall isolated yield) are necessary to procure gram quantities of the natural product. Functional group manipulations, protecting group chemistry, and unnecessary redox fluctuations have been minimized.

Synthesis, Cyclic Voltammetric Studies, and Electrogenerated Chemiluminescence of a New DonorAcceptor Molecule: 3,7-[Bis[4-phenyl-2-quinolyl]]-10-methylphenothiazine

Abstract: We report here the synthesis of a novel compound that contains two electron-accepting phenylquinoline groups covalently attached to the 3,7-positions of a light-emitting electron donor, 10-methylphenothiazine. The optimized geometry as determined from semiempirical MNDO calculations shows that the phenylquinoline moieties are twisted ∼77.5° from the phenothiazine central ring. As a result, no molecular orbital overlap between these two groups exists, inhibiting any delocalization of the charge upon electrochemical oxidation or reduction. Comparison between cyclic voltammograms obtained of this compound as well as of the individual compounds, 10-methylphenothiazine and 2-phenylquinonine, did indeed show no change in the electrochemical behavior of these two groups upon the covalent attachment, confirming the results obtained from the semiempirical calculations. A shift to lower energy wavelengths of phenothiazine was observed upon the addition of the electron-deficient phenylquinoline moieties. Overall, th...