The Journal of Organic Chemistry

New methods of formation of meta-substituted aromatic compounds

J Adams, M Belley

Index: Adams, Julian; Belley, Michel Journal of Organic Chemistry, 1986 ,  vol. 51,  # 20  p. 3878 - 3881

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Citation Number: 9

Abstract

The addition of organolithium reagents to the oxa tricyclic ketone 1 occurs stereospecifically to produce the corresponding tertiary carbinols 2a-d. When the alcohols 2a-d are treated with Tic&, ring fragmentation and dehydration occur to produce good yields of 5, 6- dihydrobenzaldehydes 3a-d. Oxidation of aldehydes 3a-d then leads to the corresponding meta-substituted benzaldehydes 4a-d. Alternatively, use of the Lewis acid Me, BBr did not ...