1892-12-2Relevant academic research and scientific papers
The Retro-Hydroformylation Reaction
Kusumoto, Shuhei,Tatsuki, Toshiumi,Nozaki, Kyoko
supporting information, p. 8458 - 8461 (2015/11/27)
Hydroformylation, a reaction that adds carbon monoxide and dihydrogen across an unsaturated carbon-carbon multiple bond, has been widely employed in the chemical industry since its discovery in 1938. In contrast, the reverse reaction, retro-hydroformylation, has seldom been studied. The retro-hydroformylation reaction of an aldehyde into an alkene and synthesis gas (a mixture of carbon monoxide and dihydrogen) in the presence of a cyclopentadienyl iridium catalyst is now reported. Aliphatic aldehydes were converted into the corresponding alkenes in up to 91 % yield with concomitant release of carbon monoxide and dihydrogen. Mechanistic control experiments indicated that the reaction proceeds by retro-hydroformylation and not by a sequential decarbonylation-dehydrogenation or dehydrogenation-decarbonylation process.
Photochemical Hydroxymethylation of Alicyclic and Aliphatic Alkenes Induced by a EuIII/EuII Photoredox System in Methanol
Ishida, Akito,Yamashita, Shinya,Toki, Susumu,Takamuku, Setsuo
, p. 1195 - 1200 (2007/10/02)
The photoirradiation of a methanol solution of EuCl3 and alkenes such as cyclohexene, cyclooctene, cyclododecene, and tetramethylene afforded (hydroxymethyl)alkane.The dihydro dimer of alkene,hydrogen, and ethylene glycol are also formed.Reactions proceed via a radical mechanism induced by hydrogen atoms and hydroxymethyl radicals, which are produced by a photoredoc reaction of EuIII/EuII in methanol.
