STEREOSPECIFICITY OF ALKOXYMERCURATION OF ALLENES

The ethoxymercuration of optically active 1,2-cyclononadiene with a series of mercuric salts is described. Evidence is presented for the existence of a mercurinium ion intermediate 2 and an allylic carbonium ion 3 which may be formed reversibly from 2. The stability of 2, and the relative stereospecificity of the reaction, is shown to be directly related to the mercuric salt utilized in the reaction. © 1969, American Chemical Society. All rights reserved.