58326-67-3Relevant academic research and scientific papers
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
Radical reaction of chlorophyll derivatives triggered by AIBN
Oba, Toru,Tateno, Yubi,Ihara, Misaki,Fukusumi, Takanori,Takei, Natsuki,Ito, Satoshi
, p. 725 - 727 (2014)
Radical reactions of a C3-vinylated chlorophyll derivative, methyl pyropheophorbide-a, which were induced by thiols and the conventional initiator azobisisobutyronitrile (AIBN) were examined in vitro for the first time. Thiyl radicals attacked regioselectively at the sole C3-vinyl group, and the anti-Markovnikov sulfanyl adducts were obtained as major products. The other peripheral substituents, as well as the chlorin macrocycle, remained intact. The AIBN-induced radical reaction competed with co-oxidation that afforded the C3-formyl chlorin. This method can open new routes to derivatization of vinyl chlorins.
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.
