ELECTRON-TRANSFER VS NUCLEOPHILIC-ADDITION OF KETENE SILYL ACETALS WITH HALOGENATED P-BENZOQUINONE DERIVATIVES

被引：16

作者：

FUKUZUMI, S

FUJITA, M

MATSUBAYASHI, G

OTERA, J

机构：

[1] OKAYAMA UNIV SCI, DEPT APPL CHEM, OKAYAMA 700, JAPAN

[2] OSAKA UNIV, COLL GEN EDUC, INST CHEM, TOYONAKA, OSAKA 560, JAPAN

来源：

CHEMISTRY LETTERS | 1993年 / 08期

关键词：

D O I：

10.1246/cl.1993.1451

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A beta,beta-dimethyl-substituted ketene silyl acetal reduces p-chloranil to produce the carbon-oxygen adduct, the hydrolysis of which yields the corresponding hydro-quinone ether (3). The structure of 3 has been determined by the X-ray crystal analysis. On the other hand, the reaction of a nonsubstituted ketene silyl acetal with p-fluoranil yields the carbon-carbon adduct selectively. The mechanistic difference between the C-O and C-C bond formation is elucidated based on the kinetic study.

引用

收藏

页码：1451 / 1454

页数：4

相关论文

共 13 条

[1] 2,3-DICHLORO-5,6-DICYANO-1,4-BENZOQUINONE (DDQ) OXIDATION OF SILYL ENOL ETHERS TO ENONES VIA DDQ-SUBSTRATE ADDUCTS [J].

BHATTACHARYA, A ;

DIMICHELE, LM ;

DOLLING, UH ;

GRABOWSKI, EJJ ;

GRENDA, VJ .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (26) :6118-6120

[2] DEHYDROSILYLATION VERSUS ALPHA-COUPLING IN THE ELECTRON-TRANSFER OF ENOL SILYL ETHERS TO QUINONES - STRONG SOLVENT EFFECT ON PHOTOGENERATED ION-PAIRS [J].

BOCKMAN, TM ;

PERRIER, S ;

KOCHI, JK .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1993, (04) :595-597

[3]

EVANS DH, 1978, ENCY ELECTROCHEMISTR, pCH12

[4] ELECTRON-TRANSFER OXIDATION OF KETENE SILYL ACETALS AND OTHER ORGANOSILANES - THE MECHANISTIC INSIGHT INTO LEWIS ACID MEDIATED ELECTRON-TRANSFER [J].

FUKUZUMI, S ;

FUJITA, M ;

OTERA, J ;

FUJITA, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (26) :10271-10278

[5] ONE-ELECTRON OXIDATION POTENTIALS OF AN NADH MODEL-COMPOUND AND A DIMERIC RHODIUM(I) COMPLEX IN IRREVERSIBLE SYSTEMS - A CONVENIENT DETERMINATION FROM THE FLUORESCENCE QUENCHING BY ELECTRON-ACCEPTORS [J].

FUKUZUMI, S ;

HIRONAKA, K ;

NISHIZAWA, N ;

TANAKA, T .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1983, 56 (08) :2220-2227

[6] MECHANISTIC INVESTIGATION OF THE REACTION BETWEEN ALPHA-SULFONYL CARBANIONS AND POLYHALOGENOMETHANES - ELECTRON-TRANSFER VERSUS POLAR PATHWAYS [J].

MATTALIA, JM ;

VACHER, B ;

SAMAT, A ;

CHANON, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (11) :4111-4119

[7] HOW CAN HIGH DIASTEREOSELECTIVITY BE ATTAINED IN THE MICHAEL ADDITION OF KETENE SILYL ACETALS [J].

OTERA, J ;

FUJITA, Y ;

SATO, T ;

NOZAKI, H ;

FUKUZUMI, S ;

FUJITA, M .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (19) :5054-5055

[8] LEWIS ACID-MEDIATED ALPHA-TERT-ALKYLATION OF CARBOXYLIC-ACIDS AND CARBOXYLIC ESTERS [J].

REETZ, MT ;

SCHWELLNUS, K ;

HUBNER, F ;

MASSA, W ;

SCHMIDT, RE .

CHEMISCHE BERICHTE-RECUEIL, 1983, 116 (11) :3708-3724

[9]

REHM D, 1970, ISRAEL J CHEM, V8, P259

[10]

ROTHORE R, 1993, TETRAHEDRON LETT, V34, P1859