Ion radicals. XXV. Reactions of thianthrene and phenothiazine perchlorates with nitrite ion, pyridine, and other nucleophiles

HJ Shine, JJ Silber, RJ Bussey…

Index: Shine,H.J. et al. Journal of Organic Chemistry, 1972 , vol. 37, p. 2691 - 2697

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Citation Number: 48

Abstract

Reaction of thianthrene perchlorate (1) with sodium nitrite in nitromethane solution gave thianthrene 5-oxide (2) and nitric oxide, each in greater than 90% yield. Reaction with BO- labeled nitrite ion showed that the oxygen in 2 came from the nitrite ion. Reaction of 1 with sodium nitrate gave 2 (92, 98%) and nitrogen dioxide (71, 75%). Reaction of 1 with pyridine in nitromethane solution gave 73% of N-(2-thianthrenyl) pyridinium perchlorate (3) and 90 ...