This paper reports the synthesis of two new organotin hydrides containing the (phenyldimethylsilyl)methyl ligand. It was found that the reaction of (phenyldime thylsilyl)methylmagnesium bromide in ether afforded ((phenyldimethylsilyl)methyl) trimethyltin (2) (72%), and with (-)-menthyldimethyltin bromide 3 gave (((phenyl dimethylsilyl)methyl)(1R,2R,5R)-2-isopropyl-5-methylcyclohexyl)dimethyltin (4) (84%). Bromodealkylation of 2 with bromine in MeOH led to the corresponding monobromide 5 (82%), which upon reduction with LiAlH4 yielded ((phenyldimethyl silyl)methyl)methyltin hydride (6) (95%). The best method for obtaining the corresponding bromostannylated derivative of compound 4, i.e., (((phenyldime thylsilyl)methyl)(1R,2R,5R)-2-isopropyl-5-methylcyclohexyl)methyltin bromide (7) was the exchange reaction between 4 an HgBr2 that led to 7 with 90% yield. The reduction of bromide 7 with LiAlH4 gave a diastereomers mixture of (((phenyldime thylsilyl)methyl)(1R,2R,5R)-2-isopropyl-5-methylcyclohexyl)methyltin hydride (8). Some physical properties, and 1H, 13C, and 119Sn NMR of the new organotin hydrides as well as that of their intermediate precursors are included.
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Synthesis and some physical properties of new organometallic compounds containing Si and Sn atoms
Published:
14 November 2018
by MDPI
in The 22nd International Electronic Conference on Synthetic Organic Chemistry
session General Organic Synthesis
Abstract:
Keywords: organo tin silicon compounds, tin-(-)Menthyl derivatives, organotin hydrides