INTERMOLECULAR REACTIONS OF N-ALKOXYCARBONYLIMINIUM IONS WITH PROPARGYLTRIMETHYLSILANE - OXAZINONE VERSUS ALLENE FORMATION

被引：24

作者：

ESCH, PM ^{[1
]}

HIEMSTRA, H ^{[1
]}

SPECKAMP, WN ^{[1
]}

机构：

[1] UNIV AMSTERDAM,DEPT ORGAN CHEM,NIEUWE ACHTERGRACHT 129,1018 WS AMSTERDAM,NETHERLANDS

来源：

TETRAHEDRON | 1992年 / 48卷 / 16期

关键词：

PROPARGYLSILANES; N-ACYLIMINIUM IONS; 3,4-DIHYDRO-2H-1,3-OXAZIN-2-ONES; ALLENES; BETA-SILYL CATION;

D O I：

10.1016/0040-4020(92)85018-A

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Intermolecular reactions of N-alkoxycarbonyliminium ions with propargyltrimethylsilane mainly lead to 6-(trimethylsilyl)methyl-3,4-dihydro-2H-1,3-oxazinones, formed by intramolecular trapping of a stabilized beta-silyl vinylic cation. Alpha-Allenyl carbamates are obtained as minor products. The oxazinone/allene ratio is dependent on the nature of the Lewis acid and the solvent used.

引用

页码：3445 / 3462

页数：18

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