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Abstract The present work involved the following studies: (A) Stobbe cpndeasat;ion of o-chlorcbenzaldeQde and -d ime thyl homophthalabe; o-Chlorobenzaldehyde was condensed w i k h dimebhyl homophthalate bo give c is-me thy1 M-(o-aarboxyphenyl) o-ohlor oc innamate (XLVIIIa) as the sole prod uot . The oonfigurat ion or” t h i s half-es&r was assigned from tihe following sequenoes of reac tions: (1) Its sbabilitg bowards uv-radiat ions. (2) Atibempted o y c l i s a t i o n of the a -half-es’cer (XLVIIIa) with fused zinc chloride or phosphorous oxychlor ide gave o is- b" ~ "-(o-" ~ "arboxypheny1)-0-0hlor acid anhydr ide (ILLTXa) . ’Pr eat ment; of t h i s anhydr ide with anhyds?ous aluminium ohlor ide gave 2-( o-o ar boxyphenyl)+hlo" ~ " 0inden-b" ~ "" ~ " which on deoar boxylat; ion afforded 4-chloro-2-phenylinden- 1-one (LI) .. Mebhanolysis of the anhydride gave ”ce isomeric s(- half-esber (LII) . Att;empt ed cyclisatiion of tihis <-halfe s t e r w i t h oonoentrated H2S04 at room beaperatwe or phosphor ous oxychlor ide gave back the anhydr ide (XLMa) |