21464-41-5Relevant articles and documents
Electron-transfer-induced reductive cleavage of phthalans: Reactivity and synthetic applications
Azzena, Ugo,Demartis, Salvatore,Melloni, Giovanni
, p. 4913 - 4919 (2007/10/03)
The behavior of phthalan (1a) was investigated under conditions of electron transfer from alkali metals in aprotic solvents. Reaction with lithium in the presence of a catalytic amount of naphthalene in THF led to the reductive cleavage of an arylmethyl carbon-oxygen bond, with formation of a stable dilithium compound. Trapping of this intermediate with several electrophiles (alkyl halides, carbonyl derivatives, CO2) was successful. The extension of this procedure to several substituted phthalans (1b-i) was investigated, and the regiochemistry as well as the synthetic usefulness of these reactions are discussed.
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.
Findings on 2,3-benzoxazine. VII. (1)-4-phenyl-1H-3,4-dihydro-2,3-benzozazine and derivatives
Pifferi,Consonni
, p. 949 - 962 (2007/10/05)
-