7151-68-0Relevant articles and documents
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Canzoneri
, (1880)
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Toward a better understanding on the mechanism of ortholithiation. Tuning of selectivities in the metalation of meta-anisic acid by an appropriate choice of base
Nguyen, Thi-Huu,Chau, Nguyet Trang Thanh,Castanet, Anne-Sophie,Nguyen, Kim Phi Phung,Mortier, Jacques
, p. 2445 - 2448 (2007/10/03)
(Chemical Equation Presented) If employed in THF at 0°C, LTMP metalates meta-anisic acid at the doubly activated position. In contrast, n-BuLi/t-BuOK deprotonates position C-4 preferentially at low temperature. Functionalization at C-6 requires protection of the C-2 site beforehand. As a result of these findings, a new mechanism is proposed for the heteroatom-directed ortholithiation of aromatic compounds.
Selective para metalation of unprotected 3-methoxy and 3,5-dimethoxy benzoic acids with n-butyl lithium-potassium tert-butoxide (LIC-KOR): Synthesis of 3,5-dimethoxy-4-methyl benzoic acid
Sinha, Surajit,Mandal, Bhubaneswar,Chandrasekaran, Srinivasan
, p. 3157 - 3160 (2007/10/03)
The potassium salt of 3-methoxy and 3,5-dimethoxy benzoic acids undergoes deprotonation at the position para to the carboxylate group selectively when treated with LIC-KOR in THF at -78°C and it has been extended to the synthesis of 3,5-dimethoxy-4-methyl benzoic acid. (C) 2000 Elsevier Science Ltd.