THE ETALCL(2)-CATALYZED CARGILL REARRANGEMENT OF BICYCLO[N.2.0] COMPOUNDS PREPARED BY THE [2+2] CYCLOADDITION OF CYCLOALKENONES AND 1-T-BUTYLDIMETHYLSILYL-2-METHYLTHIOACETYLENE

被引：3

作者：

NARASAKA, K

SHIMADZU, H

HAYASHI, Y

机构：

来源：

CHEMISTRY LETTERS | 1993年 / 04期

关键词：

D O I：

10.1246/cl.1993.621

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

EtAlCl2 catalyzes the Cargill rearrangement of bicyclo[n.2.0] compounds which were prepared by the TiCl4-mediated [2+2] cycloaddition reaction of cycloalkenones and 1-t-butyldimethylsilyl-2-methylthioacetylene, yielding various bicyclo[n-1.2.1] compounds under mild reaction conditions.

引用

收藏

页码：621 / 624

页数：4

相关论文

共 18 条

[1] CYCLOBUTANONES AND CYCLOBUTENONES IN NATURE AND IN SYNTHESIS [J].

BELLUS, D ;

ERNST, B .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (06) :797-827

[2] ACID-CATALYZED REARRANGEMENTS OF BETA,GAMMA-UNSATURATED KETONES [J].

CARGILL, RL ;

JACKSON, TE ;

PEET, NP ;

POND, DM .

ACCOUNTS OF CHEMICAL RESEARCH, 1974, 7 (04) :106-113

[3] ACID-CATALYZED ISOMERIZATIONS OF BETA,GAMMA-UNSATURATED KETONES [J].

CARGILL, RL ;

CRAWFORD, JW .

JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (02) :356-&

[4]

CRIMMINS MT, 1991, COMPREHENSIVE ORGANI, V5

[5]

Duc D. K. M., 1975, J CHEM SOC CHEM COMM, P282

[6] TRICYCLO[4.2.2.01,6]DECANE-TRICYCLO[4.2.2.01,5]DECANE INTERCONVERSIONS - [4.2.2]PROPELLANE REARRANGEMENTS AND A NON-PHOTOCHEMICAL PROPELLANE SYNTHESIS [J].

EATON, PE ;

JOBE, PG ;

NYI, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (21) :6636-6638

[7] ASYMMETRIC [2+2] CYCLOADDITION REACTION BETWEEN ALPHA,BETA-UNSATURATED ACID-DERIVATIVES AND ALKYNYL OR ALKENYL SULFIDES CATALYZED BY A CHIRAL TITANIUM REAGENT [J].

HAYASHI, Y ;

NARASAKA, K .

CHEMISTRY LETTERS, 1990, (08) :1295-1298

[8]

Hesse M., 1991, RING ENLARGEMENT ORG

[9] NOVEL REARRANGEMENT OF 5,6-DISUBSTITUTED BICYCLO[4.2.0]OCTAN-2-ONES WITH ALCL3 - APPLICATION TO TOTAL SYNTHESIS OF (+/-)-5-OXOSILPHIPERFOL-6-ENE AND (+/-)-SILPHIPERFOL-6-ENE [J].

KAKIUCHI, K ;

UE, M ;

TSUKAHARA, H ;

SHIMIZU, T ;

MIYAO, T ;

TOBE, Y ;

ODAIRA, Y ;

YASUDA, M ;

SHIMA, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (10) :3707-3712

[10] ELECTROCYCLIC RING OPENINGS OF DIALKYLCYCLOBUTENES - ANOMALIES EXPLAINED [J].

KALLEL, EA ;

YING, W ;

SPELLMEYER, DC ;

HOUK, KN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (19) :6759-6763