SINGLE AND DOUBLE REDUCTIVE CLEAVAGE OF C-O BONDS OF AROMATIC DIMETHYL ACETALS AND KETALS - GENERATION OF BENZYLIC MONOCARBANIONS AND DICARBANIONS

被引：14

作者：

AZZENA, U

MELLONI, G

PISANO, L

SECHI, B

机构：

[1] Dipartimento di Chimica, Università di Sassari, I-07100 Sassari

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 36期

关键词：

D O I：

10.1016/S0040-4039(00)73488-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reductive cleavage of aromatic dimethyl acetals and ketals, 1, with Li metal in THF at low temperature allows the generation of stable alpha-alkoxy-alpha-arylsubstituted carbanions, avoiding the Wittig rearrangement. Reaction of these carbanions with various electrophiles afforded the expected products 2. Further in situ reaction of compounds 2 afforded the products of reductive electrophilic disubstitution, 3.

引用

收藏

页码：6759 / 6762

页数：4

相关论文

共 14 条

[1] WITTIG REARRANGEMENT OF AROMATIC ACETALS AND KETALS INDUCED BY REDUCTIVE ELECTRON-TRANSFER [J].

AZZENA, U ;

DENURRA, T ;

MELLONI, G ;

PIRODDI, AM .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (20) :5532-5535

[2]

AZZENA U, 1993, TETRAHEDRON LETT, V35, P5635

[3] ELABORATION OF ALPHA-SUBSTITUTED BENZYL ETHERS AND SULFIDES BY SUPPRESSION OF THE WITTIG AND RELATED REARRANGEMENTS [J].

DAVIES, SG ;

HOLMAN, NJ ;

LAUGHTON, CA ;

MOBBS, BE .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (22) :1316-1317

[4] REDUCTIVE OPENING OF 2-PHENYL-1,3-DIOXOLANES BY A NAPHTHALENE-CATALYZED LITHIATION - SYNTHETIC APPLICATIONS [J].

GIL, JF ;

RAMON, DJ ;

YUS, M .

TETRAHEDRON, 1993, 49 (42) :9535-9546

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

GUIJARRO, D ;

MANCHENO, B ;

YUS, M .

TETRAHEDRON, 1993, 49 (06) :1327-1334

[6]

HOFFMANN RW, 1972, LIEBIGS ANN CHEM, P725

[7] 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

[8]

KATRITZKY AR, 1987, SYNTHESIS-STUTTGART, P415

[9] DIRECT ORTHO-METALATION OF BENZYL ALCOHOLS - A NOVEL METHOD OF PREPARING ORTHO-SUBSTITUTED BENZYL ALCOHOLS [J].

MEYER, N ;

SEEBACH, D .

CHEMISCHE BERICHTE-RECUEIL, 1980, 113 (04) :1304-1319

[10] SYNTHETICALLY USEFUL DIANIONS VIA REDUCTIVE LITHIATION OF TETRAHYDROFURANS BY AROMATIC RADICAL-ANIONS [J].

MUDRYK, B ;

COHEN, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (05) :1866-1867