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.
引用
收藏
页码:4241 / 4246
页数:6
相关论文
共 46 条
[1]   REACTION OF HEXAMETHYLPHOSPHORIC TRIAMIDE WITH ALKYLLITHIUMS - INSITU FORMATION OF N-METHYLMETHYLENIMINE [J].
ABATJOGLOU, AG ;
ELIEL, EL .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (20) :3042-3043
[2]  
AVIGNAC P, 1974, TETRAHEDRON LETT, P2651
[3]   METALATION AND ELECTROPHILIC SUBSTITUTION OF AMINE DERIVATIVES ADJACENT TO NITROGEN - ALPHA-METALLO AMINE SYNTHETIC EQUIVALENTS [J].
BEAK, P ;
ZAJDEL, WJ ;
REITZ, DB .
CHEMICAL REVIEWS, 1984, 84 (05) :471-523
[4]   STABLE SIMPLE ENOLS .5. SOLVENT DEPENDENCE OF THE CONFORMATION OF THE OH GROUP IN 2,2-DIMESITYLETHENOL AND SEVERAL 1,2,2-TRIARYLETHENOLS [J].
BIALI, SE ;
RAPPOPORT, Z .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (19) :5641-5653
[5]   STABLE SIMPLE ENDS .19. STERIC EFFECTS AND THRESHOLD ROTATIONAL MECHANISMS IN 1-SUBSTITUTED 2,2-DIMESITYLETHENOLS [J].
BIALI, SE ;
NUGIEL, DA ;
RAPPOPORT, Z .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (03) :846-852
[6]  
BIALI SE, 1985, J ORG CHEM, V90, P3918
[7]   REACTIONS INVOLVING ELECTRON TRANSFER .1. REDUCTION OF 2,2,6,6-TETRAMETHYL-4-HEPTEN/3-ONE [J].
BOWERS, KW ;
GIESE, RW ;
GRIMSHAW, J ;
HOUSE, HO ;
KOLODNY, NH ;
KRONBERG.K ;
ROE, DK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (09) :2783-&
[8]   INVESTIGATIONS ON ORGANOGERMANIUM COMPOUNDS .11. PREPARATION AND STRUCTURE OF TRIALKYLGERMYL ALKALI METAL COMPOUNDS IN HEXAMETHYLPHOSPHORIC TRIAMIDE ]HMPT) [J].
BULTEN, EJ ;
NOLTES, JG .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1971, 29 (03) :397-&
[9]  
COURET J, 1973, J ORGANOMET CHEM, V47, P67
[10]  
CRUTCHFIELD MM, 1967, 31P NUCLEAR MAGNETIC, P173