74145-07-6Relevant academic research and scientific papers
Direct ortho-Metalation of Benzyl Alcohols. A Novel Method of Preparing ortho-Substituted Benzyl Alcohols
Meyer, Norbert,Seebach, Dieter
, p. 1304 - 1319 (2007/10/02)
Benzyl alcohol and other phenylcarbinols (8a - 11a), including α-tetralol (12a), are doubly deprotonated by excess n-butyllithium/TMEDA in pentane to give lithium ortho-lithioalkoxides (2, 8b - 12b).Alkylations (-> 3a - d, table 1), reactions with heteroelectrophiles (-> 3e - k, table 2) and with carbonyl compounds (-> 6, 13 - 17, tables 3 and 4), as well as subsequent reactions of the primary adducts (-> phthalanes 7, table 3) furnish a large variety of ortho-substituted benzyl alcohol derivatives.The scope and limitations of the dilithioorganyls (sections B and C), their mode of formation (section A), and attempts to doubly metalate 2-phenylethanol are discussed.
