Peri fluoro steric effects: syntheses and comparative acid-catalyzed isomerization of the 8-, 9-, and 11-fluoro-1, 2, 3, 4-tetrahydro-7, 12-dimethylbenz [a] anthracenes to …

DT Witiak, S Goswami, GE Milo

Index: Witiak, Donald T.; Goswami, Shyamaprosad; Milo, George E. Journal of Organic Chemistry, 1988 , vol. 53, # 2 p. 345 - 352

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Citation Number: 17

Abstract

Facile and regiospecific syntheses for &, 9-, and ll-fluoro-1, 2, 3, 4-tetrahydro-7, 12- dimethylbenz [a] anthracenes (4, 5, and 7) from 5, 6, 7, 8-tetrahydro-l-naphthaldehyde and the respective 2-(2-fluoro-6-iodopheny1) oxazoline 14, 2-(2-bromo-5-fluorophenyl) oxazoline 15, and 2-(3-fluorophenyl) oxazoline 16 are described. Comparative acid- catalyzed isomerization of these polycyclic aromatic hydrocarbons (PAH) to exo ...