Photochemical retro-aldol type reactions of nitrobenzyl derivatives. Mechanistic variations in the elimination of nitrobenzyl carbanions from nitrobenzyl derivatives on photolysis

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Abstract
The photochemical retro-aldol type reactions of several nitrobenzyl derivatives are reported. The reactions are observed only in aqueous solution with quantum efficiencies being pH dependent for several derivatives, consistent with the existence of several mechanistic pathways for reaction. The primary photochemical event is believed to involve the generation of a nitrobenzyl carbanion, which acts as a photolabile leaving group in these reactions, and the generation of an oxocarbocation (or oxocarbocation-derived) fragment.

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