24149-63-1Relevant academic research and scientific papers
A New Photochemical Synthesis of Dihydropyrazoles. Novel Mode of Photocyclization of Some 1-Iminobut-3-enes Derivatives
Armesto, Diego,Horspool, William M.,Mancheno, Maria J.,Ortiz, Maria J.
, p. 721 - 722 (1993)
While some hydrazine derivatives 3 of 2,2-dimethyl-4,4-diphenylbut-3-enal undergo both the aza-di-?-methane (ADPM) rearrangement and a novel cyclization to afford dihydropyrazole derivatives 5 in varying yields, the tosylhydrazone derivative of 3,3-dimethyl-5,5-diphenylpent-4-en-2-one 7 gives exclusively an excellent yield of the corresponding dihydropyrazole 8, in a reaction that is proposed to involve an electron transfer process.
The oxa-di-π-methane rearrangement of β,γ-unsaturated aldehydes
Armesto, Diego,Ortiz, Maria J.,Ramano, Santiago
, p. 965 - 968 (1995)
As far as we are aware, there are only two examples of oxa-di-π-methane (ODPM) rearrangement with β,γ-unsaturated aldehydes. However, we have discovered four other cases of this reaction, taking place with 1-methyl-3-phenyl-2-cyclohexene-1-carbaldehyde, 1
Influence of electron-donor sensitizers on SET-promoted photochemical reactions of β,γ-unsaturated aldehydes
Armesto, Diego,Ortiz, Maria J.,Agarrabeitia, Antonia R.,Martin-Fontecha, Mar
, p. 2261 - 2264 (2007/10/03)
β,γ-Unsaturated aldehydes undergo photochemical oxa-di-π-methane and decarbonylation reactions using DMN as an electron-donor sensitizer, whereas, using DMA, other photoproducts resulting from proton abstraction by ketyl- and alkene-centered radical-anion
Photochemical reactivity of 1-substituted-1-aza-1,4-dienes promoted by electron-acceptor sensitizers. Di-π-methane rearrangements and alternative reactions via radical-cation intermediates
Armesto, Diego,Ortiz, Maria J.,Agarrabeitia, Antonia R.,Aparicio-Lara, Santiago,Martin-Fontecha, Mar,Liras, Marta,Martinez-Alcazar, M. Paz
, p. 9397 - 9405 (2007/10/03)
Irradiation of a series of β,γ-unsaturated imines, oxime acetates, and oxime methyl ethers, using 9,10-dicyanoanthrathene (DCA) or dicyanodurene (DCD) as electron acceptor sensitizers, affords the corresponding cyclopropanes resulting from 1-aza-di-π-methane rearrangements via radical cations. In some cases, alternative reactions of these intermediates occur to yield nitriles, dihydroquinolines, dihydronaphthalene derivatives, and cycloaddition products. Some of these products result from reactions via alkene radical-cation intermediates while others arise by pathways involving imine radical-cation intermediates. The yields of products formed in these processes were significantly higher when DCD was used as electron-acceptor sensitizer instead of DCA.
Novel photochemical behaviour of the oximes and hydrazones of β,γ-unsaturated carbonyl compounds
Armesto, Diego,Ramos, Ana,Ortiz, Maria J.,Horspool, William M.,Mancheno, Maria J.,Caballero, Olga,Mayoral, Elena P.
, p. 1535 - 1541 (2007/10/03)
A study of the photochemical reactivity of a series of β,γ-unsaturated oximes and hydrazone derivatives under triplet sensitized conditions has been carried out. The oximes 3c, 4a and 4c cyclize to the corresponding dihydroisoxazoles 5c, 6a and 6c while t
Unexpected oxadi-π-methane rearrangement of β,γ-unsaturated aldehydes
Armesto, Diego,Ortiz, Maria J.,Romano, Santiago,Agarrabeitia, Antonia R.,Gallego, Mar G.,Ramos, Ana
, p. 1459 - 1466 (2007/10/03)
The oxadi-π-methane rearrangement (ODPM) is considered to represent the normal photochemical behavior of β,γ-unsaturated ketones in the triplet excited π,π* state. However, the usual photoreactivity reported for the majority of β,γ-unsaturated aldehydes i
Chemically Efficient Aza-Di-?-Methane Photoreactivity with Novel Stable Derivatives of β,γ-Unsaturated Carbonyl Compounds
Armesto, Diego,Horspool, William M.,Mancheno, Maria J.,Ortiz, Maria J.
, p. 2325 - 2330 (2007/10/02)
The syntheses of new stable derivatives of β,γ-unsaturated carbonyl compounds such as 2,2-dimethyl-4,4-diphenylbut-3-enal 6 and 3,3-dimethyl-5,5-diphenylpent-4-en-2-one 7 are described.The majority of these derivatives undergo efficient aza-di-?-methane r
Extension of the Aza-di-?-methane Reaction to Stable Derivatives. Photochemical Cyclization of β,γ-Unsaturated Oxime Acetates
Armesto, Diego,Horspool, William M.,Langa, Fernando,Ramos, Ana
, p. 223 - 228 (2007/10/02)
The successful sensitized photochemical conversion of oxime acetates of some β,γ-unsaturated aldehydes and of one ketone into cyclopropane derivatives by the aza-di-?-methane (ADPM) rearrangement has been carried out.Thus, for example, the acetophenone-se
The Aza-di-?-methane Rearrangement of Stable Derivatives of 2,2-Dimethyl-4,4-diphenylbut-3-enal
Armesto, Diego,Horspool, William M.,Mancheno, Maria J.,Ortiz, Maria J.
, p. 2348 - 2349 (2007/10/02)
The sensitised irradiations of the semicarbazone (7a), the benzoylhydrazone (7b), and the oxime benzoate (7c) of 2,2-dimethyl-4,4-diphenylbut-3-enal afford the corresponding derivatives of 2,2-dimethylcyclopropanecarbaldehyde (8a-c) in good yield by an az
