O-Quinonemethide intermediates and their role in coordinated reactions of magnesium phenoxides with. alpha.-branched aliphatic aldehydes

G Casnati, A Pochini, MG Terenghi…

Index: Casnati, Giuseppe; Pochini, Andrea; Terenghi, Maria Giuliana; Ungaro, Rocco Journal of Organic Chemistry, 1983 , vol. 48, # 21 p. 3783 - 3787

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Citation Number: 18

Abstract

The reactions of (ary1oxy) magnesium bromides with a-branched aliphatic aldehydes in apolar solvents have been investigated in order to obtain information on the role of 0- quinone methide intermediates 8 or 9 in controlling the selectivity of the reactions of phenolic substrates and carbonyl compounds, which usually give a complex mixture of products. These reactions are characterized by high ortho regioselectivity, giving 2, 2'- ...