Abstract
The addition of phosphorous tribromide or thionyl chloride to compounds of the type R 3SiCH 2CD 2OH (where R 3 = Me 3, PhMe 2, Ph 2Me or Ph 3) gave rise to approximately the same proportion of the α-deuteriated product R 3SiCH 2CD 2X and the β-deuteriated product R 3SiCD 2CH 2X in all cases. Fragmentation accompanied the rearrangement, the yields of breakdown products R 3SiX, decreased with successive phenyl substitution on silicon and little or no decomposition was observed with (2-hydroxyethyl-2,2- d 2)triphenylsilane, Ph 3SiCH 2CD 2OH. The compounds trimethyl(2-methyl-2-hydroxypropyl)silane (Me 3SiCH 2CMe 2OH) and trimethyl(2,2-diphenyl-2-hydroxyethyl)silane (Me 3SiCH 2CPh 2OH) did not give the expected products with phosphorous tribromide or thionyl chloride, complete decomposition to trimethylsilyl halide and olefin being observed.
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