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Phthalides and 1,3-indandione. XIII. Reactions of 2-phenyl-1,3-indandiones and 2-(α-naphthyl)-1,3-indandiones with monohalo- and dihaloacetate ethyl esters

M. Furdík, V. Vačoková, and P. Hrnčiar

Komensky University, Bratislava

Abstract: The mechanism of the reaction of the title compds. was studied. A phthalide with NaOEt was converted to the Na salt of indandione, which in abs. EtOH reacted with the corresponding mono- or dihaloacetate ester. The following compds. were prepd.: Et (2-phenyl-1,3-dioxoindan-2-yl)acetate, m. 105°, Et (2-phenyl-1,3-dioxoindan-2-yl)chloroacetate, m. 119-20°, Et (2-phenyl-1,3-dioxoindan-2-yl)bromoacetate, m. 146-7°, Et bis(2-phenyl-1,3-dioxoindanyl)acetate, m. 103-4°, Et [2-(α-naphthyl)-1,3-dioxoindan-2-yl]acetate, m. 109-10° and Et bis[2-(α-naphthyl)-1,3-dioxoindan-2-yl]acetate, m. 183-4°. The first stage of the reaction with Et dihaloacetates is bimol. (SN2), and the second stage, that is the substitution of the second halogen atom with a 2-phenyl-1,3-dioxoindanyl or with a 2-(α-naphthyl)-1,3-dioxoindanyl residue, is, because of steric hindrance, unimol. (SN1). This is also proven by the fact that the second stage of the reaction of 2-phenyl-1,3-indandione with Et dibromoacetate does not occur under reflux in EtOH, but does occur in BuOH at a temp. 40° higher. In the second stage, the more bulky α-naphthyl group favors the loss of the Br anion from the first reaction product.

Full paper in Portable Document Format: 167a532.pdf (in Slovak)

Chemical Papers 16 (7) 532–541 (1962)