TY - JOUR
T1 - Catalysis by cobalt compounds of aldol and retroaldol reactions
AU - Tencer, Y.
AU - Michman, M.
AU - Goldenfeld, I.
PY - 1991/7/16
Y1 - 1991/7/16
N2 - Aldol condensation of acetone, butanone, and 2-pentanone, and retroaldol reaction of neat diacetone alcohol and 3-methyl-3-hydroxyheptan-5-one are catalyzed by (Ph3P)3CoCH3 and (Ph3P)3CoSi(CH3)3. The condensations are reversible and the retroaldol reaction is favoured. Several hindered or cyclic ketones, such as higher homologues, 3-pentanone, methyl isopropyl ketone or cyclohexanone do not condense. By comparison, aliphatic aldehydes react fast and irreversibly to yield products comprised of three aldehyde units. (Ph3P)3CoCH3 also catalyzes protium/deuterium scrambling between ketones and acetone-d6. This exchange takes place preferably at the C3 carbon whereas condensation takes place at the C1 carbon. The reactions take place at 20°C or below, and of the several organometallic compounds tested only the two mentioned above were found to be active.
AB - Aldol condensation of acetone, butanone, and 2-pentanone, and retroaldol reaction of neat diacetone alcohol and 3-methyl-3-hydroxyheptan-5-one are catalyzed by (Ph3P)3CoCH3 and (Ph3P)3CoSi(CH3)3. The condensations are reversible and the retroaldol reaction is favoured. Several hindered or cyclic ketones, such as higher homologues, 3-pentanone, methyl isopropyl ketone or cyclohexanone do not condense. By comparison, aliphatic aldehydes react fast and irreversibly to yield products comprised of three aldehyde units. (Ph3P)3CoCH3 also catalyzes protium/deuterium scrambling between ketones and acetone-d6. This exchange takes place preferably at the C3 carbon whereas condensation takes place at the C1 carbon. The reactions take place at 20°C or below, and of the several organometallic compounds tested only the two mentioned above were found to be active.
UR - http://www.scopus.com/inward/record.url?scp=3142609703&partnerID=8YFLogxK
U2 - 10.1016/0022-328X(91)86055-U
DO - 10.1016/0022-328X(91)86055-U
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AN - SCOPUS:3142609703
SN - 0022-328X
VL - 412
SP - 203
EP - 214
JO - Journal of Organometallic Chemistry
JF - Journal of Organometallic Chemistry
IS - 1-2
ER -