Effect of Electron Withdrawing Substituents in OsO4 Reactions and Pinacol-Pinacolone Reaction

EFFECT OF ELECTRON WITHDRAWING SUBSTITUENTS IN OSO4 REACTIONS AND PINACOL-PINACOLONE REARRANGEMENTS 

Pandey et were the first to study the effect of electron- 

In order to investigate the effect of various electron-withdrawing groups at different positions of the macrocycle on the migratory aptitudes of the pinacol-pinacolone 

217R = 0, R =N-Hexyl or R = N-Hexyl, R = O (mixture of four isomers) 

From these studies, it can be concluded that it is not a simple matter to define the general substituent migratory aptitudes in chloiin and bacteriochlorin systems, because distant conjugated peripheral substituents can dramatically affect the stability of carbocation intermediates and hence the products. The facility of the rearrangement of various substituents depends not only on the intrinsic nature of the migratory group but also on the electronic and steric factors present elsewhere on the tetrapyrrolic systems. 

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E. Effect of Electron Withdrawing Substituents in OSO4 Reactions and Pinacol-Pinacolone Reaction. 190... 

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