A COMPLEX INDUCED PROXIMITY EFFECT IN THE ANIONIC FRIES REARRANGEMENT OF ORTHO-IODOPHENYL BENZOATES - SYNTHESIS OF DIHYDRO-O-METHYLSTERIGMATOCYSTIN AND OTHER XANTHONES

被引：31

作者：

HORNE, S

RODRIGO, R

机构：

[1] WILFRID LAURIER UNIV,DEPT CHEM,WATERLOO N2L 3C5,ONTARIO,CANADA

[2] UNIV WATERLOO,DEPT CHEM,WATERLOO N2L 3G1,ONTARIO,CANADA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 15期

关键词：

D O I：

10.1021/jo00302a011

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

: The success of an anionic Fries rearrangement, used to synthesise dihydro-O-methylsterigmatocystin and other xanthones, is dependent on the presence of a remote methoxyl substituent. © 1990, American Chemical Society. All rights reserved.

引用

页码：4520 / 4522

页数：3

共 10 条

[1] STEREOCONTROL AND REGIOCONTROL BY COMPLEX INDUCED PROXIMITY EFFECTS - REACTIONS OF ORGANOLITHIUM COMPOUNDS [J].

BEAK, P ;

MEYERS, AI .

ACCOUNTS OF CHEMICAL RESEARCH, 1986, 19 (11) :356-363

[2] FROM CRYSTAL STATICS TO CHEMICAL-DYNAMICS [J].

BURGI, HB ;

DUNITZ, JD .

ACCOUNTS OF CHEMICAL RESEARCH, 1983, 16 (05) :153-161

[3]

COLE RJ, 1970, TETRAHEDRON LETT, P3109

[4] PLANAR TETRACOORDINATE CARBON-ATOMS HIDDEN IN THE TETRAMERIC AGGREGATE OF (2,6-DIMETHOXYPHENYL)LITHIUM [J].

HARDER, S ;

BOERSMA, J ;

BRANDSMA, L ;

VANHETEREN, A ;

KANTERS, JA ;

BAUER, W ;

SCHLEYER, PV .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (23) :7802-7806

[5] THE MOLECULAR-STRUCTURE OF 1-LITHIO-2-METHOXYBENZENE IN THE SOLID-STATE AND IN SOLUTION [J].

HARDER, S ;

BOERSMA, J ;

BRANDSMA, L ;

VANMIER, GPM ;

KANTERS, JA .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1989, 364 (1-2) :1-15

[6] CARBANIONICALLY INDUCED [1,3]-MIGRATIONS OF PI-GROUP AND COORDINATIVELY UNSATURATED GROUP [J].

HELLWINKEL, D ;

LAMMERZAHL, F ;

HOFMANN, G .

CHEMISCHE BERICHTE-RECUEIL, 1983, 116 (10) :3375-3405

[7] THE REGIOSPECIFIC PARA-DEIODINATION OF 2,4-DI-IODO PHENOLS - A NEW SYNTHESIS OF AFLATOXIN-B2 [J].

HORNE, S ;

WEERATUNGA, G ;

RODRIGO, R .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (01) :39-41

[8] STUDIES IN XANTHONE SERIES .8. AN UNAMBIGUOUS SYNTHESIS OF JACAREUBIN [J].

JEFFERSO.A ;

SCHEINMA.F .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1966, (02) :175-&

[9] THE METAL-PROMOTED FRIES REARRANGEMENT [J].

MILLER, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (02) :322-323

[10]

RANCE MJ, 1969, TETRAHEDRON LETT, P277, DOI 10.1016/S0040-4039(01)87529-8

← 1 →