58326-67-3Relevant articles and documents
A mild conversion from 3-vinyl- to 3-formyl-chlorophyll derivatives
Oba, Toru,Uda, Yuki,Matsuda, Kohei,Fukusumi, Takanori,Ito, Satoshi,Hiratani, Kazuhisa,Tamiaki, Hitoshi
, p. 2489 - 2491 (2011)
The C3-vinyl group of a chlorophyll derivative, methyl pyropheophorbide-a, was converted into the formyl group by a novel one-pot reaction with thiophenol at room temperature. The mild reaction can provide insight into development of 'green' catalysts dis
Ene-thiol reaction of C3-vinylated chlorophyll derivatives in the presence of oxygen: Synthesis of C3-formyl-chlorins under mild conditions
Fukusumi, Takanori,Takei, Natsuki,Tateno, Yubi,Aoki, Takuya,Ando, Ai,Kozakai, Kouhei,Shima, Hiroko,Mizoguchi, Tadashi,Ito, Satoshi,Ikeda, Tsukasa,Tamiaki, Hitoshi,Oba, Toru
, p. 1188 - 1195 (2013)
Reactions of thiol with the C3-vinyl group of various chlorophyll (Chl) derivatives were examined. The reactions resemble thiol-olefin co-oxidation, except that the vinyl C=C double bond was cleaved to afford a formyl group without any transition metal catalyst, and that the simple anti-Markovnikov adduct of thiol to olefin was obtained as a minor product. Peripheral substituents of Chl derivatives little affected the reaction, while the central metal atom of the chlorin macrocycle influenced the composition of the products. Oxygen and acid dissolved in the reaction mixture can facilitate the oxidation. Sufficiently mild conditions in this regioselective oxidation at the C3 1-position are significant in bioorganic chemistry.
