Dichlorocarbene-induced deamination of naphthalen-1, 4-imines and anthracen-9, 10-imines

…, CS LeHoullier, JT Eaton, NR Easton Jr…

Index: Gribble, Gordon W.; Allen, Robert W.; LeHoullier, Craig S.; Eaton, Jefferson T.; Easton, N. Roy; et al. Journal of Organic Chemistry, 1981 , vol. 46, # 5 p. 1025 - 1026

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Citation Number: 2

Abstract

corresponding aromatic hydrocarbons using mild oxidizing conditions (usually m- chloroperbenzoic acid), a reaction that may involve cheletropic extrusion4 of a nitrosoalkane from the derived arenimine oxide. We now report that dichlorocarbene, generated under phase-transfer conditions by using the Makosza method: efficiently converts 9-methyl-l, 4- dihydronaphthalen-1, 4-imines (1) and 11-methyl-1, 2, 3, 4-tetrachloro-9, lO-di- ...