Synthesis of Silyl Dienes and Silyl Indenes from Propargyl Silanes

RTU 59. Studentu zinātniskā un tehniskā konference: tēžu krājums 2018
Mikus Puriņš, Māris Turks

Here we report the use of strong Brønsted acids such as triflic acid to protonate the triple bond in propargyl silanes. Resulting β-silyl vinyl carbenium ion undergoes 1,2-silyl shift to give more stable β-silyl allyl carbenium ion. Allyl carbenium ions generated from terminal propargyl silanes undergo deprotonation to give silyl dienes. For 1-aryl propargyl silanes a competing intramolecular Friedel-Crafts alkylation in the intermediate carbenium ion is observed. Careful investigation of reaction conditions revealed that more polar solvents and less coordinating acid anion favor silyl indene formation.

Keywords
Propargyl silane, Bronsted acid, silyl diene, silyl indene, 1,2-silyl shift

Puriņš, M., Turks, M. Synthesis of Silyl Dienes and Silyl Indenes from Propargyl Silanes. In: RTU 59. Studentu zinātniskā un tehniskā konference: tēžu krājums, Latvia, Rīga, 27-27 April, 2018. Rīga: 2018, pp.1-1.

Publication language
Latvian (lv)