Tetrahedron

New homologation of 2-hydroxy and 2-mercapto benzylic alcohols

PK Choudhury, J Almena, F Foubelo, M Yus

Index: Almena, Juan; Foubelo, Francisco; Yus, Miguel Tetrahedron, 1995 , vol. 51, # 11 p. 3351 - 3364

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Citation Number: 29

Abstract

The reaction of benzo-1, 3-dioxanes or benzo-1, 3-oxathianes 1 [easily prepared from 2- hydroxy or 2-mercapto benzylic alcohols (3 or 4, respectively) and carbonyl compounds] with an excess of lithium and a catalytic amount of DTBB (4.5 mol%) in THF at room temperature or− 78° C leads, after hydrolysis with water, to the corresponding homobenzylic alcohols 2. Cyclisation of compounds 2 under acidic (85% H3PO4) or neutral (Ph3P/DIAD ...