Hydrophenanthrene synthesis via an environmentally friendly chromium carbene-alkyne coupling process

ORGN 358

Rongti Li1, Lei Zhang, lezhang@nmsu.edu1, Alejandro Camacho-Davila, alcamach@nmsu.edu1, James W. Herndon, jherndon@nmsu.edu2, and Karen Cress1. (1) Department of Chemistry & Biochemistry, New Mexico State University, MSC 3C, Las Cruces, NM 88003, (2) Department of Chemistry and Biochemistry, New Mexico State University, MSC 3C, Las Cruces, NM 88003

The reaction of gamma,delta-unsaturated carbene-chromium complexes with 2-alkynylbenzoyl systems has been examined in an aqueous environment.  When this coupling was conducted in water in the presence of surfactants, efficient formation of hydrophenthrenes and deposition of chromium hexacarbonyl onto the condenser was noted, thus allowing for a net process that is substoichiometric in chromium.  Additional examples of this reaction related to the synthesis of abietane diterpenes will also be presented.