TY - JOUR
T1 - Synthesis of 4,4-dimethyl-3,5-bis-(diphenylphosphino)cyclohexanone
AU - Zabotina, E.Y.
AU - De Kanter, F.J.J.
AU - Bickelhaupt, F.
AU - Wife, R.L.
PY - 2001
Y1 - 2001
N2 - The title diphosphine 1 has been synthesized by double Michael addition of diphenylphosphine to 4,4-dimethyl-2,5-cyclohexadienone (2). NMR spectroscopy revealed that instead of the desired cis adduct 1a, which is of interest as a bidentate ligand for transition metal centers, the trans isomer 1b had been obtained. This was rationalized by analyzing the stereochemistry of intermediates in this reaction. Attempted conversion of 1b to the thermodynamically more stable 1a by oxidation to the bisphosphine oxide 5 followed by base catalyzed equilibration was thwarted by decomposition in the second step. © 2001 Elsevier Science Ltd. All rights reserved.
AB - The title diphosphine 1 has been synthesized by double Michael addition of diphenylphosphine to 4,4-dimethyl-2,5-cyclohexadienone (2). NMR spectroscopy revealed that instead of the desired cis adduct 1a, which is of interest as a bidentate ligand for transition metal centers, the trans isomer 1b had been obtained. This was rationalized by analyzing the stereochemistry of intermediates in this reaction. Attempted conversion of 1b to the thermodynamically more stable 1a by oxidation to the bisphosphine oxide 5 followed by base catalyzed equilibration was thwarted by decomposition in the second step. © 2001 Elsevier Science Ltd. All rights reserved.
UR - https://www.scopus.com/pages/publications/0035905126
UR - https://www.scopus.com/inward/citedby.url?scp=0035905126&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(01)01043-2
DO - 10.1016/S0040-4020(01)01043-2
M3 - Article
SN - 0040-4020
VL - 57
SP - 10177
EP - 10180
JO - Tetrahedron
JF - Tetrahedron
IS - 51
ER -
