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5. Solution structure of some [[lambda].sup.3] iodanes: An [super 17]O NMR and DFT study

Author

Mocci, Francesca, Uccheddu, Gianluca, Frongia, Angelo, and Cerioni, Giovanni

Subjects
Density functionals -- Usage, Benzoic acid -- Structure, Benzoic acid -- Spectra, Nuclear magnetic resonance spectroscopy -- Usage, Biological sciences, Chemistry
Abstract

The investigation of the structure of a series of I-O bonded bis(acyloxy)iodoarenes and benzoiodoxolones in chloroform solution, which was carried out by using [super 17]O NMR spectroscopy and density functional theory (DFT) calculations is presented.

Published
2007

7. Photochemical Transformation Of A 1,2-Dihydropyridin-3-One: An Original Tandem Retro-[4+2]/[2+2] Cycloaddition Process

Author

Aitken, David J., Frongia, Angelo, Gaucher, Xavier, Ollivier, Jean, Rafique, Hummera, Sambiagio, Carlo, and Secci, Francesco

Abstract

The UV irradiation of N-benzyl-2-phenyl-1,2-dihydropyridin-3-one furnished trans-1-benzyl-4-phenyl-3-vinylazetidin-2-one, a structural isomer, as the main product. A novel tandem mechanism involving a [4+2] photocycloreversion followed by a Staudinger cycloaddition reaction is proposed, and is supported with the trapping of the purported vinylketene intermediate by other imines. This process predominates in the presence of ethylene, precluding the formation of an intermolecular [2+2] cyclobutane adduct. (C) 2013 Elsevier Ltd. All rights reserved.

Published
2013

8. Analoghi di sintesi del feromone sessuale come strumento per il controllo della popolazione di Lymantria dispar

Author

Bernard, Angela Maria, Cerboneschi, Anna, Crnjar, Roberto Massimo, Frongia, Angelo, Liscia, Anna Maria, Masala, Carla, Secci, F., Piras, Pier Paolo, Solari, Paolo, and Sollai, Giorgia

Subjects
CHIM/06 Chimica organica
Abstract

La strategia riproduttiva delle farfalle notturne è basata sull’utilizzo di un feromone speciespecifico, prodotto dagli esemplari femminili per il richiamo a lunga distanza degli individui maschi conspecifici. In particolare le femmine di Lymantria dispar, uno dei più importanti insetti fitofagi defogliatori delle sugherete sarde, elaborano un feromone costituito da un unico componente, chiamato (+)disparlure (2-methyl-7,8-epoxy-octadecane) e lo accumulano nella ghiandola del feromone fino al rilascio. Nel presente lavoro abbiamo sintetizzato diversi analoghi del feromone naturale, allo scopo di ottenere molecole con un maggiore potere attrattivo sugli esemplari maschili, o più stabili nel tempo, ossia dotate di tempi di decadimento più lunghi.

Published
2004

12. Solution structure of some lambda(3) Iodanes: an (17)O NMR and DFT study.

Author

Mocci F, Uccheddu G, Frongia A, and Cerioni G

Abstract

The structure of a series of I-O bonded bis(acyloxy)iodoarenes and benzoiodoxolones in chloroform solution has been investigated by 17O NMR spectroscopy and by density functional theory (DFT) calculations, employing the PBE0 functional together with the LANL2DZ basis set extended with polarization (d) and diffuse (p) functions. This combined approach allowed us to ascertain that, although these classes of lambda(3) iodanes maintain in chloroform solution their solid state "T-shaped" structure, a degenerate [1,3] sigmatropic shift of iodine between the two oxygens of the acyloxy groups occurs in solution. The energy barrier involved in this process differs in the two classes, thus causing significant differences in the 17O NMR spectra, at room temperature, of the two classes of compounds.

Published
2007
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