Journal of Organometallic Chemistry p. 1 - 10 (1989)
Update date:2022-09-26
Topics: Regioselectivity Green chemistry Characterization Yield NMR spectroscopy Distillation Decomposition Nucleophile reflux Deprotonation Chromatography Recrystallization Mass spectrometry (MS) Gas syringe Atom economy Electrophiles Protecting groups Deprotection GC (gas chromatography) Precursor Solvent polarity TLC (thin-layer chromatography) HPLC (high-performance liquid chromatography) Mechanistic Studies Product Isolation Workup Reaction Conditions Steric Effects Safety Precautions Reaction Mechanism Electronic effects Substrate Limitations Solvent Effects Substituent Effects Reaction Time Catalysis Catalyst Loading Reaction Monitoring Cryogenic Conditions Literature Comparison Literature Search Ethical Considerations Quenching Extraction Functional Group Interconversion Byproducts Lithiation Structural Elucidation Reaction Solvent Reaction Optimization
Cabiddu, S.
Floris, C.
Gelli, G.
Melis, S.
Direct dimetalation of 1-methyl-2-(methylthio)benzene (1) gives the dilithiated species (2) in good yield, which can be used to introduce substituents into the thiomethyl and methyl groups.Species 2 can react also with a variety of dichlorosilanes and dichlorostannanes, and with sulphur chloride, to yield derivatives of 1,3-benzothiasilin, 1,3-benzothiastannin and 1,3-benzodithiin respectively.Reaction of 2 with tetrachlorosilane yields a spirocyclic silicon compound, while reaction with benzoyl chloride yields a derivative of 1-benzothiopyran.
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