3531-47-3

Upstream product

• 507-19-7 t-butyl bromide 
• 16643-09-7 trimethylstannyl sodium 
• 507-20-0 tertiary butyl chloride 
• 558-17-8 tert-Butyl iodide 
• 38423-82-4 potassium trimethylstannate 
• 17946-71-3 lithium trimethylstannyl 
• 594-27-4 tetramethylstannane 
• 54031-00-4 1-bromo-2-((trimethylstannyl)methyl)benzene 
• 1529-47-1 chlorotrimethylgermane 

Downstream Products

• 762-84-5 N-tert-butylacetamide 
• 115-11-7 isobutene 
• 132381-82-9 5-tert-Butyl-1,2,4-Benzenetricarbonitrile 
• 58219-46-8 2-(tert-butyl)succinic acid dimethyl ester 
• 15673-05-9 4,4-dimethylvaleronitrile 
• 1066-45-1 trimethyltin(IV)chloride 
• 594-27-4 tetramethylstannane 
• 56004-15-0 dimethyl(tert-butyl)tin chloride 
• 14586-54-0 tris(1,10-phenanthroline)iron(II) perchlorate 
• 35373-52-5 (CH₃)2Sn(tert-C₄H₉)(CH(CH₃)(C₆H₅)) 

Relevant academic research and scientific papers

Selective lithiation of 1-bromo-2-((trimethylstannyl)methyl)benzene: Synthesis of 1-bromo-2-(lithiomethyl)benzene, 1-lithio-2-((trimethylstannyl)methyl)benzene, and α,2-dilithiotoluene

Reactions of 1-bromo-2-((trimethylstannyl)methyl)benzene (1) with n-butyllithium and tert-butyllithium have been investigated. With n-butyllithium in tetrahydrofuran (THF) at -70°C, the only observed process was lithium-tin exchange, yielding 1-bromo-2-(lithiomethyl)benzene (2). In contrast, lithium-halogen exchange occurred when 1 was treated with tert-butyllithium in diethyl ether at -80°C to give 1-lithio-2-((trimethylstannyl)methyl)benzene (3). α,2-Dilithiotoluene could be prepared in high yield from 3 and tert-butyllithium in either diethyl ether (room temperature) or THF (-80°C).

Nucleophilicity vs. basicity in reactions of n-butyllithium and tert-butyllithium with tetramethylstannane

The reactions of n-butyllithium and tert-butyllithium with tetramethylstannane have been examined with the objective of determining the degree of competition between proton abstraction from the methyl groups and nucleophilic displacement of these groups f

REACTIONS OF TRIMETHYLTINSODIUM WITH ALKYL HALIDES. EFFECTS OF STRUCTURE AND SOLVENT ON COURSE OF REACTION AND REACTIVITY

The reactions of eleven alkyl chlorides and bromides with trimethyltinsodium have been examined.It has been found that primary and secondary halides react smoothly and rapidly to provide good yields of substitution products in THF and TG at Oo.The reaction is less satisfactory for allyl bromide and unsatisfactory for cinnamyl chloride and tertiary halides.Trimethyltinsodium and 2-chlorobutane react with second order kinetics.Relative reactivities of the halides have been determined in the two solvents and are discussed.Lithium, sodium and potassium as counterions yielded the same results in the reaction of the trimethyltinalkils with primary, secondary and tertiary butyl bromides in THF.