Synthesis of Substituted 4-Vinyl Chromanes via Tandem 1,2-Silyl Shift – Friedel–Crafts Cyclization
RTU 65. studentu zinātniskās un tehniskās konferences tēzes 2024
Artjoms Ubaidullajevs, Rasma Kroņkalne, Krišjānis Gercāns, Māris Turks

Previously our scientific group has observed, that protonation of propargyl silanes can cause 1,2-silyl shift, which leads to the formation of relatively stable allylic cation. It can further undergo attack by internal nucleophile, affording 5-membered carbocycles (indenes) or 5-membered heterocycles (tetrahydrofuranes, pyrrolidines, tetrahydrothiophenes and isoxazolidines). In this work, the application of 1,2-silyl shift in the synthesis of 6-membered cycles was examined. A new synthetic pathway to substituted 4-vinyl chromanes was proposed, successfully employing tandem 1,2-silyl shift – Friedel–Crafts cyclization approach in the final synthetic step.


Keywords
1,2-Silyl Shift, Friedel–Crafts Cyclization, Chromanes, Propargyl Silanes

Ubaidullajevs, A., Kroņkalne, R., Gercāns, K., Turks, M. Synthesis of Substituted 4-Vinyl Chromanes via Tandem 1,2-Silyl Shift – Friedel–Crafts Cyclization. In: RTU 65. studentu zinātniskās un tehniskās konferences tēzes, Latvia, Rīga, 26-26 April, 2024. Rīga: 2024, pp.1-2.

Publication language
Latvian (lv)
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