Collect. Czech. Chem. Commun. 1996, 61, 946-950

Regioselective Tritiation of Carbamate Dicyclic Juvenoids

Tomáš Elberta, Martin Rejzekb and Henri Virelizierc

a Department of Organic Chemistry, Charles University, 128 40 Prague 2, Czech Republic
b Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic,166 10 Prague 6, Czech Republic
c DCC-DPE SPEA, Bdt. 391, CEA-Saclay, 91191 GIF-SUR-YVETTE Cedex, France


The tritiated juvenoids ethyl N-{2-[4-(cis-2-hydroxy-1-cycloheptylmethyl)phenoxy]ethyl}carbamate (1), 2-[4-(trans-2-hydroxy-1-cyclohexylmethyl)phenoxy]ethyl N-ethylcarbamate (2) and ethyl N-{2-[4-(c-2-hydroxy-3-methyl-r-1-cyclohexylmethyl)phenoxy]ethyl}carbamate (3) were prepared by Catalyzed Exchange in Solution with Gas on PdO/BaSO4. The high degree of regio- and stereoselectivity observed in the products by 3H NMR is discussed in the terms of the stereoelectronic requirements of the exchange reaction.

Keywords: CESG; 3H NMR; Tritiated juvenoids; Stereoselectivity.