Tek&cdmn L.ettws. zyxwvutsrqponmlkjihgfedcbaZYXWVUTSRQPONMLKJIHGFEDCBA Vol.32, No.19. pi 21533156.1991 PfhEdhGICdtBfith oo404039/91 $3.00 + Do Pergamml Press plc FRIFDEL-CNAFTS COORDINATBD PRDCESSBS: SBLECTIVE CYCLOOLIGOEBRIEATION zyxwvutsrqponmlkjihgfedcbaZYXWVUTSRQP OF ACYL CHLORIDES Giovanni Sartori,* Giuseppe Casnati. Franca Bigi, Davide Baraldi Istituto di Chimica Organica dell’llniversitg, Viale delle Scienze. I-43100 Par-ma. Italy , Summary - Adducts cross-condensation. AlC13.RCOCl undergo highly regioselective self- and 4-Hydroxy-2-pyrones and 2-acetyl-indan-1.3-diones are synthesized in good yields. Aliphatic acid chlorides and anhydrides undergo condensation with different carbonyl compounds affording polymeric materials’ as well as oligomers, including cyclic derivatives’ and polyhydric phenols.3 Despite the intensive studies in this area the selective oligomeriaation of acyl chlorides remains a still open problem, particularly when the cross-condensation of different substrates is involved. During our studies on the ortho-coordinated acylation of phenol salts4 our attention turned to the evaluation of the relative stability of adducts between AlC13 and various acyl chlorides, and the reactivity of these complexes toward different carbonyl derivatives.5 Now we found that A1C13.RCH2COCl adducts are able to promote strictly controlled dehydrohalogenative cross- as well as self-condensation of acyl chlorides. This study make it possible to evidence the regiochemical behaviour of the reaction solely as a function of R in RCH2COC1. SCHEME RCH,C@Cl + AlCl, 1 RCH,CCl-O*AlCl, 1 HCl + RCH-Ccl-0-AlCl, 1 2 3 3 + 1 ) zyxwvutsrqponmlkjihgfedcbaZYXWVUT 2153