FORMATION OF ALPHA-[BIS(DIMETHYLAMINO)PHOSPHORYL]-SUBSTITUTED STABLE ENOLS AND N,N-DIALKYLDIARYLACETAMIDES FROM DIARYLKETENES AND MELI IN HMPA

被引:4
作者
NADLER, EB [1 ]
ZIPORY, ES [1 ]
RAPPOPORT, Z [1 ]
机构
[1] HEBREW UNIV JERUSALEM,DEPT ORGAN CHEM,IL-91904 JERUSALEM,ISRAEL
关键词
D O I
10.1021/jo00013a031
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of an MeLi/HMPA mixture in ether with dimesityl- and mesitylphenylketene yielded the enols MesC(Ar) = C(OH)PO(NMe2)2 and MesC(Ar) = CHOH and the amides MesCH(Ar)CON(Me)R (Ar = Mes, Ph; R = Me, Et) together with other products. An initial cleavage of the HMPA by the MeLi, followed by addition of the formed anionic species (Me2N)2PO-, Me2N-, or MeN-Et to the diarylketene, is proposed.
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页码:4241 / 4246
页数:6
相关论文
共 46 条
[31]  
NORMANT JF, 1966, B SOC CHIM FR, P3601
[32]   STABLE SIMPLE ENOLS .11. EQUILIBRIUM-CONSTANTS FOR THE 1-ALKYL-2,2-DIMESITYLETHANONE SYSTEMS IN HEXANE - THE PREDOMINANCE OF STERIC EFFECTS ON KENOL VALUES [J].
NUGIEL, DA ;
RAPPOPORT, Z .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (12) :3669-3676
[33]  
PNOMAREV SV, 1978, ZH OBSHCH KHIM+, V78, P298
[34]  
Pope M.T., 1983, HETEROPOLY ISOPOLY O
[35]   REACTION BETWEEN NAH AND HEXAMETHYLPHOSPHORAMIDE (HEMPA) [J].
PRONI, A ;
ROGGERO, A ;
MAZZEI, A ;
BRUZZONE, M .
INORGANICA CHIMICA ACTA, 1977, 21 (01) :47-49
[36]   PROTON MAGNETIC-RESONANCE AND P-31 NUCLEAR MAGNETIC-RESONANCE STUDIES OF SUBSTITUTED PHOSPHOLAN-3-ONE 1-OXIDES [J].
PURDUM, WR ;
BERLIN, KD .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (19) :2904-2911
[37]   INTERACTION OF N,N-BIS(TRIMETHYLSILYL)AMINO-N'-TRIMETHYLSILYLIMINOPHOSPHINE WITH BIS(TRIMETHYLSILYL)MERCURY - A NEW ROUTE TO COMPOUNDS CONTAINING THE P-SI LINKAGE [J].
ROMANENKO, VD ;
SHULGIN, VF ;
SCOPENKO, VV ;
MARKOVSKI, LN .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (15) :808-809
[38]   ALPHA CARBANION PHOSPHORAMIDES .2. FORMATION, STABILITY AND USE IN SYNTHESIS OF CARBANIONS DERIVED FROM N-METHYL-N-BENZYL-PHOSPHORAMIDES [J].
SAVIGNAC, P ;
LEROUX, Y ;
NORMANT, H .
TETRAHEDRON, 1975, 31 (07) :877-884
[39]  
SAVIGNAC P, 1976, TETRAHEDRON LETT, P2025
[40]  
Stanger A., UNPUB