Aluminum Chloride-Catalyzed Intramolecular Allyl-Migration Reaction of Allyl(chloromethyl)silanes and Trapping of the Intermediate with Allyltrimethylsilane

Aluminum Chloride-Catalyzed Intramolecular Allyl-Migration Reaction of Allyl(chloromethyl)silanes and Trapping of the Intermediate with Allyltrimethylsilane

Allyl(chloromethyl)diorganosilanes [CH2CHCH2SiR1R2(CH2Cl), R1 = Me, Ph; R2 = Me, Ph, p-ClC6H4] in the presence of aluminum chloride undergo an allyl rearrangement reaction with allylic inversion to afford (3-butenyl)diorganochlorosilanes at room temperature. When allyltrimethylsilane was added to t...

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Veröffentlicht in:Organometallics 2004-10, Vol.23 (21), p.4910-4914
Hauptverfasser: Jung, Hoon Yi, Park, Young-Ae Whang, Yoo, Bok Ryul, Tamao, Kohei, Jung, Il Nam
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container_end_page 4914
container_issue 21
container_start_page 4910
container_title Organometallics
container_volume 23
creator Jung, Hoon Yi
Park, Young-Ae Whang
Yoo, Bok Ryul
Tamao, Kohei
Jung, Il Nam
description Allyl(chloromethyl)diorganosilanes [CH2CHCH2SiR1R2(CH2Cl), R1 = Me, Ph; R2 = Me, Ph, p-ClC6H4] in the presence of aluminum chloride undergo an allyl rearrangement reaction with allylic inversion to afford (3-butenyl)diorganochlorosilanes at room temperature. When allyltrimethylsilane was added to the reactions, the intermediate was trapped to give 1,1-dimethyl-3-(2-trimethylsilylmethyl-4-pentenyl)silacyclopentane (4) along with 3-(butenyl)dimethylchlorosilane in 40% and 18% yields, respectively. The formation of 4 can be explained by the addition reaction of allyltrimethylsilane to 1-silacyclopent-3-yl cation produced by the intramolecular cyclization of (allyl)silylmethyl cation intermediate derived from the interaction of the chloromethyl group with aluminum chloride catalyst, followed by desilylation reaction.
doi_str_mv 10.1021/om0343465
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title Aluminum Chloride-Catalyzed Intramolecular Allyl-Migration Reaction of Allyl(chloromethyl)silanes and Trapping of the Intermediate with Allyltrimethylsilane
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