C,O-DILITHIATED DIARYLMETHANOLS - EASY AND IMPROVED PREPARATION BY NAPHTHALENE-CATALYZED LITHIATION OF DIARYL KETONES AND REACTIVITY TOWARD ELECTROPHILES

被引:41
作者
GUIJARRO, D [1 ]
MANCHENO, B [1 ]
YUS, M [1 ]
机构
[1] UNIV ALICANTE,FAC CIENCIAS,DEPT QUIM ORGAN,APDO 99,E-03080 ALICANTE,SPAIN
关键词
D O I
10.1016/S0040-4020(01)85822-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The lithiation of different diaryl ketones 1 with an excess of lithium powder and a catalytic amount (8 mol %) of naphthalene in tetrahydrofuran at -30-degrees-C leads to the formation of the corresponding dianions of the type I, with Met=Li, which react with several electrophiles (E+=MeI, EtBr, PriCHO, PhCHO, cyclohexanone, MeCN) to give, after hydrolysis, the expected substituted diarylmethanols 2.
引用
收藏
页码:1327 / 1334
页数:8
相关论文
共 24 条
[1]   REDUCTION BY DISSOLVING METALS .6. SOME APPLICATIONS IN SYNTHESIS [J].
BIRCH, AJ ;
MUKHERJI, SM .
JOURNAL OF THE CHEMICAL SOCIETY, 1949, (OCT) :2531-2536
[2]   REDUCTION BY DISSOLVING METALS .2. [J].
BIRCH, AJ .
JOURNAL OF THE CHEMICAL SOCIETY, 1945, (NOV-) :809-813
[3]  
GLASER F, 1957, CHEM ZTG, V81, P822
[4]  
GUIJARRO A, IN PRESS TETRAHEDRON
[5]   NAPHTHALENE-CATALYZED LITHIATION OF DIALKYL SULFATES - A NEW ROUTE FOR ORGANOLITHIUM REAGENTS [J].
GUIJARRO, D ;
MANCHENO, B ;
YUS, M .
TETRAHEDRON LETTERS, 1992, 33 (38) :5597-5600
[6]   NAPHTHALENE-CATALYZED LITHIATION OF ALLYLIC AND BENZYLIC MESYLATES - A NEW METHOD FOR ALLYL, METHALLYL, AND BENZYL LITHIUM [J].
GUIJARRO, D ;
MANCHENO, B ;
YUS, M .
TETRAHEDRON, 1992, 48 (22) :4593-4600
[7]   REDUCTIVE METALATION OF BENZOPHENONE AND BENZALACETOPHENONE BY ALKALI METALS IN LIQUID AMMONIA AND SOME CONDENSATIONS OF THE RESULTING DIALKALI SALTS [J].
HAMRICK, PJ ;
HAUSER, CR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (02) :493-496
[8]  
Hase T. A., 1987, UMPOLED SYNTHONS
[9]   CONVERSION OF AROMATIC KETONES, BENZYL ALCOHOLS, AND ALKYL ARYL ETHERS TO AROMATIC-HYDROCARBONS WITH LITHIUM 4,4'-DI-TERT-BUTYLBIPHENYL RADICAL-ANION [J].
KARAMAN, R ;
KOHLMAN, DT ;
FRY, JL .
TETRAHEDRON LETTERS, 1990, 31 (43) :6155-6158
[10]  
KHARASCH MS, 1950, J ORG CHEM, V15, P775