CHEMOSELECTIVE RHODIUM-CARBENOID REACTION WITH THE AROMATIC NUCLEUS -AN EFFICIENT METHODOLOGY FOR 2-INDANONES, 2-TETRALONES AND 2-BENZOSUBERONES AND ITS APPLICATION IN THE SYNTHESIS OF (+ -)-AR-HIMACHALENE/

Rhodium-carbenoid species derived from rhodium acetate-catalyzed decom position of aryl alkyl alpha-diazoketones have been shown to display a chemoselective addition into the aromatic nucleus, instead of inserti on into an aliphatic C-H site. The synthetic utility of this chemosele ctive reaction is exemplified by the preparation of substituted fused aromatic systems such as 2-indanones, 2-tetralones and 2-benzosuberone s. In addition, a short and efficient synthesis of (+/-)-ar-Himachalen e, a naturally occurring sesquiterpene is realized.