The Open Organic Chemistry Journal

2008, 2 : 100-106
Published online 2008 November 17. DOI: 10.2174/1874095200801020100
Publisher ID: TOOCJ-2-100

The First Synthesis of p-Cl- and p-F-Phenylverbenene

Claudia Contreras-Celedón and Luis Chacón-García
Laboratorio de Diseño Molecular, Instituto de Investigaciones Químico Biológicas, Universidad Michoacana de San Nicolás de Hidalgo, Morelia, Michoacán, México.

ABSTRACT

The first synthesis of 4´-X-phenylverbenene (X = F and Cl) via reaction of myrtenal with 4´-X phenylmagnesium bromide and Bi(NO3)3 is described. Verbenene is formed due to the electron-withdrawing effect of the 4´-electronegative group, either fluorine or a Cl–Bi complex.

Keywords:

Myrtenal, verbenene, bismuth nitrate.