75288-21-0Relevant academic research and scientific papers
2,7-Diazabicyclo[2.2.1]heptanes: Novel asymmetric access and controlled bridge-opening
Peczkowski, Gary R.,Craven, Philip G. E.,Stead, Darren,Simpkins, Nigel S.
supporting information, p. 4214 - 4217 (2019/05/09)
Organocatalysed asymmetric Michael additions of substituted triketopiperazines to enones afford products in high yield and enantiomeric ratio (er). Further modification delivers products possessing natural product (NP) scaffolds including diazabicyclo[2.2
Chemistry of photogenerated α-hydroxy-p-nitrobenzyl carbanions in aqueous solution: Protonation vs. disproportionation
Morrison, James,Wan, Peter,Corrie, John E.T.,Munasinghe, V. Ranjit N.
, p. 586 - 597 (2007/10/03)
The photochemistry of p-nitrobenzyl derivatives 6-10 has been studied in aqueous solution as a function of pH, using product analysis, UV-vis spectrophotometry, and laser flash photolysis (LFP). The compounds were chosen with the aim of further exploring the propensity of these systems to give rise to α-hydroxy-p-nitrobenzyl carbanions on photolysis, and to study their mechanisms of subsequent reaction, α-Hydroxy-substituted carbanions are anions that cannot be readily formed using thermal routes but which are believed to have some interesting chemistry. Three methods were employed for photogenerating these carbanions: (i) decarboxylation; (ii) retro-Aldol reaction; and (iii) carbon acid deprotonation. All three methods proved to be successful using the p-nitrobenzyl chromophore. Photogenerated α-hydroxy-p-nitrobenzyl carbanions react via disproportionation, giving rise to oxidized and reduced products; simple protonation of the anion was undetectable.
1,3-Dipolar Character of Six-membered Aromatic Rings. Part 52. 2?+8? Cycloaddition Reactions of 1-Substituted 3-Oxidopyridinium Betaines
Katritzky, Alan R.,Cutler, Alan T.,Dennis, Nicolas,Sabongi, Gebran J.,Rahimi-Rastgoo, Soheila,et al.
, p. 1176 - 1184 (2007/10/02)
Dichloroketen and a series of aryl(bromo)ketens react with various 1-substituted 3-oxidopyridiniums to give novel bicyclic compounds by addition across the C(4)-O and the C(2)-O positions.Frontier-MO theory is used to rationalise the orientation of these cycloadditions.Acid-catalysed hydrolysis of the C(2)-O adducts (9) yielded 3-hydroxy-2-benzylpyridines.
