An electron spin resonance investigation of the products of the Friedel–Crafts reaction of sulphur dioxide with methylnaphthalenes
- 1 January 1986
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 11,p. 1735-1741
- https://doi.org/10.1039/p29860001735
Abstract
A series of mono-, di-, tri-, tetra-, and hexa-methylnaphthalenes, and naphthalene were reacted with AlCl3–SO2, AlCl3–SOCl2, or AlCl3–S2Cl2, using CH2Cl2 as solvent. The radical cation products produced were studied using e.s.r. 1,4-, 1,5-, and 1,8-dimethyl-, 1,2,4-trimethyl-, 1,2,3,4- and 1,3,5,7-tetramethyl-, 1,2,3,4,5,8-hexamethyl-, and octamethyl-naphthalene all gave predominantly spectra from the monomer cation radical. Naphthalene, 1- and 2-methyl- and 1,3-, 1,6-, 1,7-, 2,3-, 2,6-, and 2,7-dimethylnaphthalene gave predominantly spectra ascribed to methyl derivatives of naphtho[1,8-cd]-1,2-dithiole. Spectra from these compounds also contained a significant component which was ascribed to methylperylenes formed from the Scholl condensation of the parent compound. A species described as 3H, 10H-acenaphtho[1,2-c]-1,2-dithiete was observed as a minor product in the reactions with 1,8-dimethylnaphthalene.Keywords
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