Intermolecular reacitons of N-alkoxycarbonyliminium ions with propargyltrimethylsilane; oxazinone versus allene formation
作者:Peter M. Esch、Henk Hiemstra、W. Nico Speckamp
DOI:10.1016/0040-4020(92)85018-a
日期:1992.1
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 β-silyl vinylic cation. α-Allenyl carbamates are obtained as minor products. The oxazinone/allene ratio is dependent on the nature of the Lewis acid and the solvent used.
N-烷氧基羰基亚胺离子与炔丙基三甲基硅烷的分子间反应主要导致6-(三甲基甲硅烷基)甲基-3,4-二氢-2H-1,3-恶嗪酮,其是通过分子内捕获稳定的β-甲硅烷基乙烯基阳离子而形成的。α-烯丙基氨基甲酸酯是次要产物。恶嗪酮/丙二烯之比取决于路易斯酸和所用溶剂的性质。