Triphenylsilyl as a Protecting Group in the Synthesis of 1, 12-Heterodisubstituted p-Carboranes

…, B Reeves, Z Janoušek, P Kaszynski

Index: Douglass, Andrew G.; Pakhomov, Serhii; Reeves, Birgit; Janousek, Zbynek; Kaszynski, Piotr Journal of Organic Chemistry, 2000 , vol. 65, # 5 p. 1434 - 1441

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Citation Number: 17

Abstract

A triphenylsilyl group is used as an auxiliary in the synthesis of heterodisubstituted p- carboranes via triphenylsilyl-p-carborane (1). The preparation of 1 is statistical, but with recovery of the starting p-carborane, the effective conversion to 1 is about 90%. Carborane 1 has been easily converted to its lithium and copper derivatives, which were reacted with a range of electrophiles including alkyl halides: an aryl iodide, an acetylene bromide, and a ...