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Phthalides and 1,3-indandiones. III. Preparation of halo and nitro derivatives of α-naphthalphthalide and 2-(α-naphthyl)-1,3-indandione. The chemistry of naphthalene and 1,3-indandione

M. Furdík and P. Hrnčiar

Komensky University, Bratislava

Abstract: cf. C.A. 50, 14674e. New derivs. of 2-(α-naphthyl)-1,3-indandione (I), halogenated or nitrated on the 4-position of the naphthalene ring are synthesized with halo or nitro derivs. of α-naphthalphthalide. The following derivs. are described (substituent on the α-naphthyl group in I and m.p. given): 4-Cl (II), 212-13°; 4-Br (III), 215-16°; 4-I (IV), 204-5°; 4-NO₂ (V), 217°. The reactivity of the α-position of the naphthalene ring enhances to a great extent the reactivity of the 4-position in α-naphthalphthalide. Also new derivs. of I simultaneously halogenated and nitrated also in the position 2 on the indandione group are synthesized, for 2-Cl deriv. (respective substituted compd. and m.p. given): II, 146°; III, 143°; IV, 144°; V, 199-202°; for 2-Br deriv. (the same data): II, 145-7°; III 155-7°; IV 150-3°; V 208-11°; for 2-iodo deriv. II, 114°; III, 124°; IV, 128°; V, 149°; for 2-NO₂ deriv., II, 151-2°; III, 201-3°; IV, 156-60°; V, 165-7°. A considerable thermal instability was detd. for substituents in positions 2 on the indandione and 4 on the naphthalene rings.

Full paper in Portable Document Format: 128a464.pdf (in Slovak)

Chemical Papers 12 (8) 464–476 (1958)