AROMATIC SUBSTITUENT EFFECT ON THE STEREOSELECTIVITY OF THE GAS-PHASE ACID-INDUCED RING-OPENING IN 9,10-OXIDES DERIVED FROM TRANS-1,2,3,4,4A,10A-HEXAHYDROPHENANTHRENE

被引：9

作者：

CHINI, M

CROTTI, P

MINUTOLO, F

DEZI, E

LOMBARDOZZI, A

PIZZABIOCCA, A

RENZI, G

机构：

[1] UNIV PISA,DIPARTIMENTO CHIM BIOORGAN,VIA BONANNO 33,I-56126 PISA,ITALY

[2] UNIV CAMERINO,DIPARTIMENTO SCI CHIM,I-62032 CAMERINO,ITALY

来源：

TETRAHEDRON | 1993年 / 49卷 / 26期

关键词：

D O I：

10.1016/S0040-4020(01)87951-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The effect of the aromatic ring substituents on the product distribution of the gas-phase acid-induced ring opening of benzocondensed epoxides 2a and 2b with MeOH was examined and compared with results from methanolysis. The observed syn/anti diastereoselectivity is strictly dependent on the type of the aromatic ring substituent (6-OCH3 or 7-Br), and a very satisfactory Hammett-type linear correlation was found for both epoxides. A razionalization of the results is given.

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收藏

页码：5845 / 5858

页数：14

相关论文

共 16 条

[1] EFFECT OF ADDITIVES ON IONIC REACTION MECHANISM IN RADIOLYSIS OF METHANE [J].

AUSLOOS, P ;

LIAS, SG ;

GORDEN, R .

JOURNAL OF CHEMICAL PHYSICS, 1963, 39 (12) :3341-&

[2] EFFECT OF SUBSTITUENTS ON STEREOSELECTIVITY OF ACID-CATALYZED HYDROLYSIS OF A SERIES OF ARYLOXIRANS - NEW APPLICATION OF HAMMETT EQUATION [J].

BATTISTINI, C ;

BALSAMO, A ;

BERTI, G ;

CROTTI, P ;

MACCHIA, B ;

MACCHIA, F .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1974, (17) :712-713

[3] DIRECTIVE EFFECTS IN AROMATIC SUBSTITUTION .30. ELECTROPHILIC SUBSTITUENT CONSTANTS [J].

BROWN, HC ;

OKAMOTO, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (18) :4979-4987

[4] GAS-PHASE ACID-INDUCED RING-OPENING IN DIASTEREOISOMERIC 9,10-OXIDES DERIVED FROM TRANS-1,2,3,4,4A,10A-HEXAHYDROPHENANTHRENE [J].

CECCHI, P ;

CHINI, M ;

CROTTI, P ;

PIZZABIOCCA, A ;

RENZI, G ;

SPERANZA, M .

TETRAHEDRON, 1991, 47 (26) :4683-4692

[5] SUBSTITUENT EFFECTS ON THE REGIOSELECTIVITY AND STEREOSELECTIVITY OF GAS-PHASE ACID-INDUCED RING-OPENING IN 1-ARYLCYCLOHEXENE OXIDES [J].

CECCHI, P ;

PIZZABIOCCA, A ;

RENZI, G ;

CHINI, M ;

CROTTI, P ;

MACCHIA, F ;

SPERANZA, M .

TETRAHEDRON, 1989, 45 (13) :4227-4234

[6] SYNTHESIS AND REACTIVITY OF BENZYLIC EPOXIDES DERIVED FROM 1,2,3,9,10,10A-HEXAHYDROPHENANTHRENE - SEARCH FOR A UNIFIED MECHANISM FOR THE RING-OPENING OF 2-ARYLOXIRANES [J].

CHINI, M ;

CROTTI, P ;

MACCHIA, F .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (16) :3930-3936

[7]

CHINI M, 1990, GAZZ CHIM ITAL, V120, P733

[8]

CHINI M, 1988, GAZZ CHIM ITAL, V118, P827

[9]

CHINI M, 1991, GAZZ CHIM ITAL, V121, P197

[10] SUBSTITUENT EFFECT ON THE DIASTEREOSELECTIVITY OF THE ACID-HYDROLYSIS AND TRICHLOROACETOLYSIS OF 9,10-OXIDES DERIVED FROM TRANS-1,2,3,4,4A,10A-HEXAHYDROPHENANTHRENE - MECHANISM OF THE EPOXIDE RING-OPENING [J].

CHINI, M ;

CROTTI, P ;

FERRETTI, M ;

MACCHIA, F .

TETRAHEDRON, 1988, 44 (07) :2001-2014