The Reaction of Deactivated Napthalene Derivatives with Sulfur Trioxide

Abstract

Abstract: The reaction of sulfur trioxide with deactivated naphthalene derivatives containing an electron withdrawing substituent, viz.-CHO,-COPh,-CO₂H, and-CO₂Me, indichloromethane as the solvent has been studied by analysis of the resulting mixtures of the sulfo derivatives with ¹HNMR,Monosulfonation of 1-formylnaphthalene yields 5-S,6-S,7-Sand 8-S, in a 55: 9:6: 30 ratio, that of 1-benzoylnaphthalene 5-S,6-S and 7-S in a ratio of 83: 11: 6, and 1-nitronaphthalene only 5-S. 1-Naphthoic acid and its methyl ester upon SO₃sulfonation and aqueous work-up both yield 5-and 8-sulfonaphthoic acid in a ratio of 65: 35 and 77: 21 respectively. The initially formed peri substituted product is the intramolecular anhydride of 8-sulfo-1-naphthoic acid. All the 2-substituted naphthalenes upon SO₃sulfonation yield 5-S and 8-S.

Key words: Deactivated naphthalene derivatives, Sulfo trioxide, Sulfonation

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ZOU You-Si, LIN Jing. The Reaction of Deactivated Napthalene Derivatives with Sulfur Trioxide[J]. Chem. J. Chinese Universities, 1995, 16(11): 1727.

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The Reaction of Deactivated Napthalene Derivatives with Sulfur Trioxide

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