(TRIMETHYLSILYL)METHYL ALLYLIC SULFONES IN INTRAMOLECULAR 4+3 CYCLOADDITIONS

被引：24

作者：

HARMATA, M

HERRON, BF

机构：

[1] Department of Chemistry, University of Missouri-Columbia, Columbia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 26期

关键词：

D O I：

10.1021/jo00078a017

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of (trimethylsilyl)methyl allylic sulfones tethered to a furan with trimethylaluminum results in the formation of products derived from the intramolecular 4 + 3 cycloaddition of the corresponding allylic cations. 2,5-Disubstitution on the furan precludes the formation of cycloadducts and results in two different classes of products which apparently result from ipso or ortho attack of the allylic cation on the furan ring followed by trapping of the resulting oxonium ions by trimethylaluminum.

引用

页码：7393 / 7396

页数：4

共 23 条

[11]

HARMATA M, 1993, TETRAHEDRON LETT, P789

[12] SYNTHESIS OF 2-NORZIZAENE AND 9,10-DEHYDRO-2-NORZIZAENE "(7,7-DIMETHYL-6-METHYLIDENETRICYCLO [6.2.1.01,5]UNDEC-9-ENE) VIA INTRAMOLECULAR ALLYL CATION INDUCED CYCLOADDITION [J].