ADDITION OF DIPHENYLPHOSPHINE TO MICHAEL-TYPE OLEFINS - THE PREPARATION OF PHOSPHINE-NITRILE AND PHOSPHINE-ESTER LIGANDS

被引:35
作者
BLINN, DA [1 ]
BUTTON, RS [1 ]
FARAZI, V [1 ]
NEEB, MK [1 ]
TAPLEY, CL [1 ]
TREHEARNE, TE [1 ]
WEST, SD [1 ]
KRUGER, TL [1 ]
STORHOFF, BN [1 ]
机构
[1] BALL STATE UNIV,DEPT CHEM,MUNCIE,IN 47306
关键词
D O I
10.1016/0022-328X(90)87207-T
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The reactions of five Michael-type olefins with diphenylphosphine have been carried out. 1-Cyanocyclopentene, 1-cyanocyclohexene, and 4-t-butyl-1-cyanocyclohexene all provide the corresponding 2-diphenylphosphino-1-cyanocycloalkanes, and both methyl acrylate and ethyl methacrylate yield the corresponding 2-diphenylphosphinopropionates. For the products from 1-cyanocyclopentene and 1-cyanocyclohexene, 13C and 31P NMR data are consistent with the formation of both trans (Ph2P equatorial and CN axial) and cis (both Ph2P and CN equatorial) isomers. The morpholine amide of 3-diphenylphosphinopropionic acid has been obtained by treatment of methyl-3-diphenylphosphinopropionate with the dimethylaluminum adduct of morpholine. This phosphine, Ph2Pmorph, has been isolated as its palladium(II) complex, (Ph2Pmorph)2PdCl2. A phosphine-benzaldimine, Ph2P(CH2)3NC(H)C6H5, has been obtained by reacting Ph2P(CH2)3NH2, from the reduction of PhP(CH2)2CN, with benzaldehyde in the presence of molecular sieves. © 1990.
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页码:143 / 152
页数:10
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