2002
DOI: 10.1002/1521-3765(20020402)8:7<1730::aid-chem1730>3.0.co;2-6
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Reactions ofgem-Dibromo Compounds with Trialkylmagnesate Reagents to Yield Alkylated Organomagnesium Compounds

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Cited by 52 publications
(21 citation statements)
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References 101 publications
(15 reference statements)
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“…7,7‐Dibromobicyclo[4.1.0]heptane :26 Benzyltriethylammonium chloride (293 mg, 1.29 mmol, 2 mol %) and cyclohexane (6.08 mL, 4.93 g, 60.0 mmol) were mixed in a flask under N 2 . The suspension was cooled to 0 °C, then dichloromethane (6 mL), absolute EtOH (0.25 mL), bromoform (7.9 mL, 22.8 g, 90.3 mmol) and 50 % aqueous NaOH (30 mL) were added in succession.…”
Section: Methodsmentioning
confidence: 99%
See 1 more Smart Citation
“…7,7‐Dibromobicyclo[4.1.0]heptane :26 Benzyltriethylammonium chloride (293 mg, 1.29 mmol, 2 mol %) and cyclohexane (6.08 mL, 4.93 g, 60.0 mmol) were mixed in a flask under N 2 . The suspension was cooled to 0 °C, then dichloromethane (6 mL), absolute EtOH (0.25 mL), bromoform (7.9 mL, 22.8 g, 90.3 mmol) and 50 % aqueous NaOH (30 mL) were added in succession.…”
Section: Methodsmentioning
confidence: 99%
“…trans ‐7‐Bromobicyclo[4.1.0]heptane :26 7,7‐Dibromobicyclo[4.1.0]heptane (1.5 mL, 3.0 g, 11.9 mmol) in THF (20 mL) was cooled to −95 °C under N 2 , at which point, n ‐butyllithium (8.2 mL, 1.5 m in hexanes, 12.3 mmol) was added. The solution was stirred for 10 min, quenched with absolute EtOH (4 mL) and stirred for 1 h while allowed to warm to room temperature.…”
Section: Methodsmentioning
confidence: 99%
“…Halogen–cobalt exchange initially takes place to produce intermediate 3 . One of the silylmethyl groups on the cobalt center migrates to generate 4 with concomitant liberation of bromide 12. β‐Hydride elimination finalizes the formation of 1,1,2‐trisilylethene 2 .…”
Section: Methodsmentioning
confidence: 99%
“…Warming the solution to room temperature resulted in (copper catalyzed) alkyl migration with resulting electrophilic quenching yielding -functionalized -silyl pentane. A different reactivity was witnessed for the methyl homologue LiMgMe3, with only the monomethylated bromo product being observed [65]. This distinction was at-tributed to the greater reactivity of intermediate A over LiMgMe3, meaning that A preferentially abstracts a bromine atom from R3SiCHBr2 to generate the monomethylated product as demonstrated in the top pathway of Figure 24.…”
Section: Uses In Metal-halogen Exchange Reactionsmentioning
confidence: 96%