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Reductive Coupling of Aromatic Aldehydes Promoted by an Aqueous TiCl 3 / t BuOOH System in Alcoholic Cosolvents
Author(s) -
Clerici Angelo,
Greco Cosimina,
Panzeri Walter,
Pastori Nadia,
Punta Carlo,
Porta Ombretta
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700252
Subject(s) - chemistry , radical , aqueous solution , medicinal chemistry , alcohol , organic chemistry , electron transfer , photochemistry
The tert ‐butoxyl radical, generated by the aqueous Ti III /TBHP system, abstracts an H atom from alcoholic cosolvents (EtOH, i PrOH), leading to α‐hydroxyalkyl radicals thatreduce aromatic aldehydes to the corresponding 1,2‐diols. The reactivities observed are explained by resonance stabilization of the α‐hydroxybenzyl radicals formed in the electron‐transfer (ET) process. Good Hammett‐type correlations are obtained. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)