Intramolecular Diels-Alder reactions of furans with a merely strain-activated tetrasubstituted alkene: Bicyclopropylidene

被引：51

作者：

Heiner, T

Kozhushkov, SI

Noltemeyer, M

Haumann, T

Boese, R

deMeijere, A

机构：

[1] UNIV GOTTINGEN,INST ORGAN CHEM,D-37077 GOTTINGEN,GERMANY

[2] UNIV GOTTINGEN,INST ANORGAN CHEM,D-37077 GOTTINGEN,GERMANY

[3] UNIV ESSEN GESAMTHSCH,INST ANORGAN CHEM,D-45117 ESSEN,GERMANY

来源：

TETRAHEDRON | 1996年 / 52卷 / 37期

关键词：

D O I：

10.1016/0040-4020(96)00720-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bicyclopropylidene derivatives 1, 6, 8 with furan moieties attached on tethers of various length and nature all undergo clean intramolecular Diels-Alder reactions with complete endo-diastereoselectivities when heated to 70 - 130 degrees C, under 10 kbar pressure. The reaction rates are at]east as high or higher than those of analogously tethered methylenecyclopropane-furan derivatives 15, 17, 20, in spite of the fact that the reactive double bond in bicyclopropylidene is tetrasubstituted and not activated by any electron withdrawing group. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：12185 / 12196

页数：12

共 20 条

[1] NITRONE AND NITRILE OXIDE CYCLOADDITIONS TO BICYCLOPROPYLIDENE - REARRANGEMENT OF THE ISOXAZOLIDINE ADDUCTS TO 3-SPIROCYCLOPROPANE-4-PYRIDONE DERIVATIVES [J].