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Please use this identifier to cite or link to this item: http://hdl.handle.net/1807/11168

Title: Microwave-assisted Thermolysis of ortho-substituted Aroylsilanes
Authors: Tremblay, Marc
Advisor: Dong, Vy Maria
Department: Chemistry
Keywords: acylsilanes
Brook rearrangement
cyclopropanation
cyclopropane
siloxycarbenes
thermolysis
aroylsilanes
microwaves
carbenes
cyclopropenation
cyclopropenes
chromanone
C-H insertion
Issue Date: 30-Jul-2008
Abstract: Microwave-Assisted Thermolysis of ortho-Substituted Aroylsilanes Marc Tremblay Master of Science Department of Chemistry University of Toronto 2008 The microwave-assisted thermolysis of ortho-substituted aroylsilanes has been investigated. When irradiated at 250ºC in DMSO or o‑dichlorobenzene for 10 minutes, aroylsilanes form siloxycarbenes that react following different pathways depending on the solvent and the structure of the starting material. It is shown that in the case of substrates having an O‑allyl or an O‑propargyl chain ortho to the acylsilane, cycloaddition occurs followed by a cascade ring opening to give respectively chroman‑4-one and chromen‑4-one derivatives in up to 66% yield. Among the major competitive pathways were the insertion of the siloxycarbene into allylic C–H bonds and decomposition of the acylsilane group to the corresponding aldehyde, followed by Claisen rearrangement.
URI: http://hdl.handle.net/1807/11168
Appears in Collections:Master
Department of Chemistry - Master theses

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