SOLVOLYSES IN SUBSTITUTED CYCLOPROPYLCARBINYL SYSTEMS .9. SOLVOLYSIS OF DISPIRO-CYCLOPROPYL-INDANOLS

The solvolyses in aqueous perchloric acid medium of yclopropane-1,1'-i ndane-3',1''-cyclopropane]-2'-ol 3a and yclopropane-1,1'-indane-2',1'' -cyclopropane]-3'-ol 4a are described. Both these alcohols undergo mod ifications at one cyclopropanic ring vicinal to the hydroxyl group. Fo r the alcohol 3a, the ratio between the ring enlargement product and t he ring opening product was 1.6:1, while for alcohol 4a the ring openi ng reaction was dominant (about 95%). A reaction mechanism was suggest ed. The synthesis of the solvolysed alcohols and the characterisation of the resulting products is given.