Jung, HY Park, YAW Yoo, BR Tamao, K Jung, IN 2024-01-21T06:10:45Z 2024-01-21T06:10:45Z 2021-09-04 2004-10-11 0276-7333 https://pubs.kist.re.kr/handle/201004/137138 Allyl(chloromethyl)diorganosilanes [CH2=(CHCH2SiRR2)-R-1(CH2Cl), R' = Me, Ph; R-2 = 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. English AMER CHEMICAL SOC FRIEDEL-CRAFTS ALKYLATION ORGANOSILICON COMPOUNDS ORGANIC-SYNTHESIS SILICON REARRANGEMENTS ALLYLSILYLATION ALLYLSILANES DERIVATIVES ALKENYL(CHLOROMETHYL)SILANES 5-SILYL-1-ALKENES Aluminum chloride-catalyzed intramolecular allyl-migration reaction of allyl(chloromethyl)silanes and trapping of the intermediate with allyltrimethylsilane Article 10.1021/om0343465 1 ORGANOMETALLICS, v.23, no.21, pp.4910 - 4914 ORGANOMETALLICS 23 21 4910 4914 scie scopus 000224348900019 2-s2.0-6344243626 Chemistry, Inorganic & Nuclear Chemistry, Organic Chemistry Article FRIEDEL-CRAFTS ALKYLATION ORGANOSILICON COMPOUNDS ORGANIC-SYNTHESIS SILICON REARRANGEMENTS ALLYLSILYLATION ALLYLSILANES DERIVATIVES ALKENYL(CHLOROMETHYL)SILANES 5-SILYL-1-ALKENES Allyltrimethylsilane Allyl(chloromethyl)silanes Aluminum Chloride Allyl-migration but-3-enylsilane