Anatomy of phobanes. Diastereoselective synthesis of the three isomers of n-butylphobane and a comparison of their donor properties

M Carreira, M Charernsuk, M Eberhard…

Index: Carreira, Monica; Charernsuk, Manutsavin; Eberhard, Michael; Fey, Natalie; Ginkel, Roel van; et al. Journal of the American Chemical Society, 2009 , vol. 131, p. 3078 - 3092

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Citation Number: 23

Abstract

Three methods for the large scale (50− 100 g) separation of the secondary phobanes 9- phosphabicyclo [3.3. 1] nonane (s-PhobPH) and 9-phosphabicyclo [4.2. 1] nonane (a- PhobPH) are described in detail. Selective protonation of s-PhobPH with aqueous HCl in the presence of a-PhobPH is an efficient way to obtain large quantities of a-PhobPH. Selective oxidation of a-PhobPH in an acidified mixture of a-PhobPH and s-PhobPH is an efficient ...