16938-99-1Relevant academic research and scientific papers
Regiospecific Introduction of Amino-alkene Functionality into 1,2,3-Triols, 1,3-Dihalogenopropan-2-ols, and 2,3-Dihalogenopropanols promoted by Fluoride Anion
Shimizu, Makoto,Yoshioka, Hirosuke
, p. 689 - 690 (2007/10/02)
Regiospecific transformations of 1,2,3-triol, 1,3-dihalogenopropan-2-ol, and 2,3-dihalogenopropanol derivatives into oxazolidin-2-ones and/or oxazol-2(3H)-ones promoted by fluoride anion are described.
ETUDE EXPERIMENTALE ET THEORIQUE DE LA PHOTOLYSE DE DERIVES DU CYCLE PYRAZOLONE
Cardy, H.,Poquet, E.
, p. 2279 - 2286 (2007/10/02)
When irradiated in protic solvents such as water and primary alcohols, pyrazolinone derivatives undergo photocleavage between the two nitrogen atoms.Substituting the C-4 atom with an electronegative group stabilizes the open chain which is obtained but a thermal transposition takes place from the linear intermediate when C-4 carries a hydrogen atom or a methyl group.The STO/3G ab initio scheme was used to study the photocleavage and the influence of the C-4 substituent, giving evidence of a mechanism which involves triplet excited states of the ?, ?* type.
Specific Enolates from α-Amino Ketones
Garst, Michael E.,Bonfiglio, John N.,Grudoski, David A.,Marks, Jeffrey
, p. 2307 - 2315 (2007/10/02)
The enolization of 11 tertiary α-amino ketones was investigated under three different conditions (kinetic base, thermodynamic base, thermodynamic acid) to determine the directionality of such enolates for application to alkaloid synthesis.The ketone structural variables examined were the geometry of the amine nitrogen lone pair-carbonyl array and the electronic nature of the nitrogen substituent.With the exception of 3-pyrrolidinones, increasing the electron-withdrawing nature of the nitrogen increases the amount of enolization toward nitrogen (3, 6, and 9 or 21, 24, and 27).N-Alkyl-substituted amino ketones (3, 12, 21, 33) under kinetic base conditions yield enolate distributions similar to those of the corresponding all-carbon compounds.N-Carbamato-substituted amino ketones (6, 24, 27, 30) enolize predominantly toward nitrogen under all conditions.The 3-pyrrolidinones 12, 15, and 18 afford enolates away from nitrogen under all conditions.
