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

Article type: Research Article

Authors: Yamamoto, Yasushi | Shimizu, Hideaki | Matui, Chinami | Chinda, Michiru

Affiliations: Silicone-Electronic Materials Research Center, Shin-Etsu Chemical Co., Ltd., 1-10 Hitomi, Matsuida, Gunma 379-02, Japan | Gunma Complex, Shin-Etsu Chemical Co., Ltd., 2-13- lsobe, Annaka, Gunma 379-01

Note: [] Corresponding author

Note: [] Corresponding author

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.

DOI: 10.1080/13583149612331338737

Journal: Main Group Chemistry, vol. 1, no. 4, pp. 409-414, 1996