10.1021/jo00392a021
The research focuses on the photoaddition of alkenes to N-methyl-1,8-naphthalimide (NMN) in methanol, resulting in the formation of novel tetracyclic imides. The study aimed to understand the mechanism behind the formation of these adducts, which was proposed to involve photostimulated electron transfer from the alkene to NMN, followed by radical coupling and addition of methanol to the resultant radical cation-radical anion pair. The researchers used a variety of chemicals in their experiments, including α-methylstyrene (α-MS), 1,1-diphenylethylene, pentadeuterio-α-methylstyrene (16), and 1,1-diphenylethene (DPE), to establish the regiochemistry and stereochemistry of the reaction. The conclusions drawn from the study provided evidence supporting the proposed mechanism and highlighted the significant impact of π-conjugation on the reactivity of aromatic imides in photochemical reactions.
10.1246/bcsj.56.3527
The research investigates the reaction of various olefins with malonic acid in the presence of manganese(III) acetate (MA) to synthesize substituted 2,7-dioxaspiro[4.4]nonane-1,6-diones and other related compounds. The purpose is to develop a convenient one-step synthesis method for these compounds, which have potential applications in organic chemistry. Key chemicals used include olefins such as 1,1-diphenylethene, 1,1-bis(4-methoxyphenyl)ethene, methylenecyclohexane, 2-phenylpropene, styrene, 1-octene, and cyclohexene, along with malonic acid and manganese(III) acetate. The reactions were carried out in acetic acid, and the products were characterized using techniques like IR spectroscopy, H-NMR spectroscopy, and HPLC. The study concludes that this method provides a straightforward and efficient route to synthesize the target compounds, with yields ranging from 3% to 84% depending on the specific olefin used. The configurations of the products were determined based on H-NMR spectral analyses, and the results showed that the reaction outcomes varied significantly depending on the substituents on the olefins.
10.1246/cl.1987.2251
The study investigates the dimerization of 1,1-diphenylethylene (1) and its derivatives using tris(p-bromophenyl)aminium hexachloroantimonate (3) as a new method to generate the cation radical. In dry solvents, 1 reacts with 3 to form indan dimer 2, while in wet solvents, butadiene derivative 7 and tetrahydrofuran derivative 8 are produced. The dimerization of derivatives like 1,1-diphenylpropene (4), 1,1-diphenyl-3-methyl-1-butene, 1,1,2-triphenylethylene (5), and 1,1-di-p-anisylethylene (6) yields different products, such as butadiene type dimer 9 from 4 in wet solvents, and cyclobutane type dimers 10, 11 from 5 and 12, 13 from 6. The study suggests that the substituents on 1,1-diphenylethylene and the methods for generating the cation radical are crucial for the types of dimers produced, though the exact reasons for the variant products remain unclear.