911804-11-0Relevant academic research and scientific papers
Photochemical δ-Hydrogen Abstraction from Acyclic and Semicyclic Monothioimides
Sakamoto, Masami,Tohnishi, Masakazu,Fujita, Tsutomu,Watanabe, Shoji
, p. 347 - 351 (2007/10/02)
Photochemical δ-hydrogen abstraction from acyclic and semicyclic monothioimides have been studied.Photolysis of acyclic monothioimides possessing a benzylic hydrogen atom at the δ-position gave γ-lactams, via a 1,5-diradical intermediate, accompanied by thioamides were generated by γ-hydrogen abstraction.Irradiation of the five-membered semicyclic monothioimide, N-(3-phenylpropionyl)pyrrolidine-2-thione, yielded 5-mercapto-4-phenyl-1-azabicyclooctan-2-one.For N-(3-phenylbutyryl)pyrrolidine-2-thione, disproportionation, involving 1,6-hydrogen migration, was the main path.Photolysis of the six-membered semicyclic monothioimide, N-(3-phenylbutyryl)piperidine-2-thione, gave an unsaturated thiol, via a 1,4-hydrogen shift of a 1,5-diradical intermediate, accompanied by cyclisation product and piperidine-2-thione.
