Substituent effects at the origin of a free-radical 1, 2-aryl migration and in the related disproportionation reaction of 10-hydro-9-pX-phenyl-9-phenanthryl radicals

RN Goerner Jr, PN Cote…

Index: Goerner,R.N. et al. Journal of Organic Chemistry, 1977 , vol. 42, # 1 p. 19 - 28

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Citation Number: 8

Abstract

A series of (9-pX-phenyl-9-fluoreny1) acetaldehydes (5)(X= H, F, Cl, OCH3, SCH3, SOCH3, S02CH3, and CHs) have been synthesized, characterized, and decarbonylated in the presence and absence of benzyl mercaptan to yield (9-pX-phenyl-9-fluoreny1) carbinyl radicals (U.). In the presence of mercaptan, these radicals rearranged to yield 9, 10-dihydi* o- 9-pX-phenylphenanthrenes (7) and 9-pX-phenyl phenanthrenes (6), and abstracted ...

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