Reaction of Raney nickel with alcohols
…, WJ Crooks III, B Zorc, SE Milczanowski
Index: Krafft, Marie E.; Crooks, William J.; Zorc, Branka; Milczanowski, Stephen E. Journal of Organic Chemistry, 1988 , vol. 53, # 14 p. 3158 - 3163
Full Text: HTML
Citation Number: 33
Abstract
The reaction of Raney nickel with a variety of functional groups was studied. Ethers, esters, and alkyl chlorides were found to be stable to Raney nickel in refluxing toluene; however, alcohols were found to be reactive. Primary alcohols were oxidized to aldehydes and then subsequently decarbonylated, secondary alcohols were oxidized to the corresponding ketone, and tertiary alcohols were deoxygenated.
Related Articles:
Carbonyl methylenation of easily enolizable ketones
[Hibino, Jun-ichi; Okazoe, Takashi; Takai, Kazuhiko; Nozaki, Hitosi Tetrahedron Letters, 1985 , vol. 26, # 45 p. 5579 - 5580]
[Ingold, K. U.; Walton, J. C. Journal of the American Chemical Society, 1987 , vol. 109, # 23 p. 6937 - 6943]
[Petasis, Nicos A.; Bzowej, Eugene I. Journal of the American Chemical Society, 1990 , vol. 112, # 17 p. 6392 - 6394]
[Lebel, Helene; Davi, Michael; Diez-Gonzalez, Silvia; Nolan, Steven P. Journal of Organic Chemistry, 2007 , vol. 72, # 1 p. 144 - 149]
Wittig type methylenation of ketones with bis (iodozincio) methane and ionic liquid
[Yoshino, Hideaki; Kobata, Masami; Yamamoto, Yuhei; Oshima, Koichiro; Matsubara, Seijiro Chemistry Letters, 2004 , vol. 33, # 9 p. 1224 - 1224]