1969
DOI: 10.1016/s0022-328x(00)81121-3
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The halogen-metal interconversion of aryl bromides and n-butyllithium in non-polar solvents

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Cited by 26 publications
(3 citation statements)
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“…The first step of the procedure is the synthesis of the tri- and tetracarbanionic initiators based on the halogen−lithium exchange reaction. As described previously, the tetrabromo compound ( 1 ) is modified to give the corresponding tetraalkyllithium agent ( 2 ), and importantly for this synthesis, lithium 2-methoxyethoxide ( 3 ) was utilized to solubilize the polyalkyllithium species due to the σ/μ complex formed between the lithiated species ( 2 and 3 ) . These complexes give stable species and enough steric bulk to prevent aggregation of the polylithiated initiators.…”
Section: Resultsmentioning
confidence: 99%
“…The first step of the procedure is the synthesis of the tri- and tetracarbanionic initiators based on the halogen−lithium exchange reaction. As described previously, the tetrabromo compound ( 1 ) is modified to give the corresponding tetraalkyllithium agent ( 2 ), and importantly for this synthesis, lithium 2-methoxyethoxide ( 3 ) was utilized to solubilize the polyalkyllithium species due to the σ/μ complex formed between the lithiated species ( 2 and 3 ) . These complexes give stable species and enough steric bulk to prevent aggregation of the polylithiated initiators.…”
Section: Resultsmentioning
confidence: 99%
“…10 Anisoyllithium was prepared by the methods of Berree et al 40 and used as a 0.43 M ethereal solution, while (p-bromophenyl)lithium was prepared by the methods of Trepka and Sonnenfeld used as a 0.37 M ethereal solution. 41 BOP was prepared by the methods of Castro. 42 Thiopyridyl chloroformate was used as a 0.19 M solution in CH2Cl2 and prepared according the methods of Corey.…”
Section: Methodsmentioning
confidence: 99%
“…Similar yields of the corresponding 4-arylcubyl iodides were achieved when p -biphenyllithium (→ 6 ) and 2-naphthyllithium (→ 7 ) were employed. Use of the doubly lithiated aromatic 1,4-dilithiobenzene, prepared by halogen−metal exchange between p -dibromobenzene and excess t -BuLi, gave p -bis(4-iodocubyl)benzene ( 8 ) in 70% isolated yield. Similarly, reaction of diiodocubane with 1,3-dilithiobenzene 13 gave the meta isomer 9 .…”
mentioning
confidence: 99%