STRUCTURE AND CONFORMATION OF ALPHA'-DIPHENYLPHOSPHINOYL ENONES - X-RAY STRUCTURE OF E-(5SR,6SR)-3,6-DIMETHYL-5-DIPHENYLPHOSPHINOYL-7-TRIPHENYLMETHOXYHEPT-2-EN-4-ONE

被引:6
作者
DOYLE, MJ [1 ]
HALL, D [1 ]
RAITHBY, PR [1 ]
SKELTON, N [1 ]
WARREN, S [1 ]
机构
[1] UNIV CAMBRIDGE,CHEM LAB,LENSFIELD RD,CAMBRIDGE CB2 1EW,ENGLAND
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 04期
关键词
D O I
10.1039/p19930000517
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of alpha'-diphenylphosphinoyl enones has been prepared and their s-cis or s-trans conformations correlated with H-1 NMR and IR spectra and an X-ray crystal structure of the title compound. The effect of chelation to cerium(III) is correlated with the regio- and stereo-selectivity of reductions under the Luche conditions.
引用
收藏
页码:517 / 523
页数:7
相关论文
共 29 条
[1]   INFRARED SPECTROSCOPY OF CARBONYL COMPOUNDS .2. EFFECT OF ALKYL SUBSTITUTION AND STEREOCHEMISTRY ON NU(C=O) AND NU(C=C) STRETCHING FREQUENCIES OF ALIPHATIC AND ALICYCLIC ALPHA-ETHYLENE KETONES WITH 6-MEMBERED AND HIGHER-MEMBERED CHAINS [J].
BARLET, R ;
MONTAGNE, M ;
ARNAUD, P .
SPECTROCHIMICA ACTA PART A-MOLECULAR SPECTROSCOPY, 1969, A 25 (06) :1081-&
[2]  
BHACCA NS, 1964, TETRAHEDRON LETT, P3127
[3]   THE STEREOCONTROLLED HORNER-WITTIG REACTION - SYNTHESIS OF DISUBSTITUTED ALKENES [J].
BUSS, AD ;
WARREN, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (11) :2307-2325
[4]   REARRANGEMENTS OF A CATION OF NEOPENTYL-TYPE CONTAINING A DIPHENYLPHOSPHINYL SUBSTITUENT [J].
CANN, PF ;
HOWELLS, D ;
WARREN, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1972, (03) :304-&
[5]   REVERSED STEREOCHEMICAL CONTROL IN THE REGIOSELECTIVE REDUCTION OF HINDERED DIPHENYLPHOSPHINOYL (PH2PO-) KETONES AND ENONES [J].
ELLIOTT, J ;
HALL, D ;
WARREN, S .
TETRAHEDRON LETTERS, 1989, 30 (05) :601-604
[6]   LANTHANOIDS IN ORGANIC-SYNTHESIS .6. THE REDUCTION OF ALPHA-ENONES BY SODIUM-BOROHYDRIDE IN THE PRESENCE OF LANTHANOID CHLORIDES - SYNTHETIC AND MECHANISTIC ASPECTS [J].
GEMAL, AL ;
LUCHE, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (18) :5454-5459
[7]   CONFORMATIONS OF SOME ALPHA-BETA-UNSATURATED CARBONYL-COMPOUNDS .3. INFRARED SOLUTION SPECTRA OF METHYL, [H-2-3]METHYL, ETHYL, AND [H-2-5]ETHYL ACRYLATES AND TRANS-CROTONATES [J].
GEORGE, WO ;
HASSID, DV ;
MADDAMS, WF .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1972, (04) :400-&
[8]   SYNTHESIS OF Z-ALLYLIC ALCOHOLS WITH 1,4-RELATED CHIRAL CENTERS BY STEREOSELECTIVE EPOXIDATION AND THE HORNER-WITTIG REACTION [J].
HALL, D ;
SEVIN, AF ;
WARREN, S .
TETRAHEDRON LETTERS, 1991, 32 (48) :7123-7126
[9]  
HANESSIAN S, 1973, TETRAHEDRON LETT, P3555
[10]   CONFORMATIONAL-ANALYSIS .122. CONFORMATIONS, ENERGIES, AND ELECTRONIC ABSORPTION-SPECTRA OF ALPHA,BETA-UNSATURATED ALDEHYDES AND KETONES [J].
LILJEFORS, T ;
ALLINGER, NL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (10) :2745-2749