Sterically induced methoxyl migration on acid-catalyzed dehydration of K-region trans-dihydrodiol monomethyl ethers

NT Nashed, TVS Rao, DM Jerina

Index: Nashed, Nashaat T.; Rao, Tata Venkata S.; Jerina, Donald M. Journal of Organic Chemistry, 1993 , vol. 58, # 23 p. 6344 - 6348

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Citation Number: 17

Abstract

The regioisomers of the trans-dihydrodiol monomethyl ethers (DME) at the K-regions of 4- and 7-methyl-and 7, 12-dimethylbenz [aIanthracene, which possess a ring methyl substituent peri to the methoxyl group, react with BFretherate to form a single phenol and two regioisomeric phenol methyl ethers, one of which arises by migration of the methoxyl group. In contrast, for DME of benz [a]-anthracene and its 1-, 4-, 7-, 11-and 12-methyl-and ...