Transformation of Oxiranes to β-Trimethylsilyloxyalkyl Iodide by N-(Trimethylsilyl) diethylamine and Methyl Iodide

Abstract

Transformation of oxiranes to β-trimethylsilyloxyalkyl iodide by use of N-(trimethylsily1)-diethylamine and two equiv of methyl iodide is described. Terminal oxiranes ^R-CH-CH₂ (R = C₆H₁₃,C₈H₁₇, CH₂ = CH(CH₂)₂, PhO and MeO) gave 1-iodo-2-trimethylsilyloxy derivatives R-CH(OsiMe₃)-CH₂I as major products in high ields along with l-trimethylsilyloxy-2-iodo derivatives R-CHI CH₂OSiM₃, while ^{C₈F₁₇CH₂-CH-CH₂} and 1,2-epoxy-cyclohexane gave selectively C₈F₁₇CH₂CH(OSiMe₃)-CH₂I and trans-1-iodo-2-trimethylsilyloxycyclohexane, respectively. Allyl bromide combined with N-(trimethylsily1) diethylamine was also effective to open an oxirane ring.