The Journal of Organic Chemistry

An unusual synthesis of 5-methoxy-7, 12-dimethylbenz [a] anthracene

MS Newman, A Kumar

Index: Newman, Melvin S.; Kumar, Arvind Journal of Organic Chemistry, 1986 , vol. 51, # 12 p. 2379 - 2380

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Citation Number: 3

Abstract

This unexpected result evidently occurs by an ipso-type electrophilic attack of the benzylic cation produced from 4 on the carbon bearing the 1-methoxy group of the naphthalene ring to form 5. The cation, 5, then stabilizes itself by loss of methanol from adjacent carbons and a proton to produce 6. To our knowledge this reaction represents the first example of an ipso- type displacement of a methoxy groups on carbons5 It is noteworthy that an ipso attack ...