42902-94-3Relevant academic research and scientific papers
Photolysis of Regioisomeric α,α-Diphenyl-Substituted Diazotetrahydrofuranones: Primary and Secondary Photochemical Processes
Rodina,Galkina,Supurgibekov,Grigor'Ev, Ya. M.,Utsal'
experimental part, p. 1542 - 1545 (2011/02/26)
The formation of C-H insertion products in the course of direct photolysis of α,α-diphenylsubstituted diazo ketones of the tetrahydrofuran series was rationalized by secondary photochemical processes which give rise to benzophenone acting as a sensitizer. Triplet excited states of diazo ketones generated by the action of benzophenone are capable of undergoing bimolecular transformations.
Surprising secondary photochemical reactions observed on conventional photolysis of diazotetrahydrofuranones
Nikolaev, Valerij A.,Galkina, Olesja S.,Sieler, Jochim,Rodina, Ludmila L.
experimental part, p. 2713 - 2716 (2010/06/19)
The formation of C-H insertion products of the terminal N-atom of a diazo group into the α-S{cyrillic}N{cyrillic}-bond of tetrahydrofuran during direct photolysis of regioisomeric 2,2-dimethyl-5,5-diphenyl and 5,5-dimethyl-2,2-diphenyl-substituted 3-diazotetrahydrofuran-4-ones in THF is dictated by photochemical cycloelimination of the originally formed (1,1-dimethyl-2-oxa-3,3-diphenyl-propano)ketene and oxetanecarboxylic acid derivatives to yield benzophenone. The latter, under subsequent UV irradiation of the reaction mixture, initiates sensitized photolysis of the starting diazoketones resulting in the appearance of the insertion products with the solvent.
γ-Silylated α,ss-unsaturated amides - Preparation by [1,5]-sigmatropic rearrangement and use as masked dienolate equivalents in carbonyl condensations
Green, James R.,Alo, Babajide I.,Majewski, Marek,Snieckus, Victor
experimental part, p. 745 - 759 (2009/12/04)
The reaction of lithium dienolates derived from N,N-dialkylsenecioamides (1a-1c) with triorganosilyl electrophiles occurs initially at the oxygen atom predominantly, and is followed by an O → C silicon migration to afford the γ-silylated senecioamides (4a-4h). The γ-silylated senecioamide Z-4a undergoes fluoride-ion-mediated condensations with aromatic aldehydes to give kinetic α-(6) and thermodynamic γ-(5) condensation product patterns comparable to lithium dienolates. The TiCl4-mediated reactions with aldehydes gives a-products (6) in a highly syn-selective manner. Possible transitionstate models for the syn-selective condensations are discussed and a chair-like transition state featuring bidentate coordination to titanium (11) is proposed.
