Beilstein J. Org. Chem.2014,10, 1942–1950, doi:10.3762/bjoc.10.202
resulted from an unexpected benzyl to o-tolyl rearrangement. The proportion of benzylversuso-tolyl derivatives depended on the reaction conditions. Benzylmagnesium chloride afforded predominantly o-tolyl carbinols while the application of benzylmagnesium bromide led preferably to the o-tolyl carbinols
possible mechanism for the Grignard reaction leading to the benzyl→o-tolyl rearrangement is also proposed.
Keywords: aldehyde; benzylversuso-tolyl; carbohydrate; Grignard reaction; rearrangement; X-ray crystallography; Introduction
One of the most popular synthetic routes leading to the formation of
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Graphical Abstract
Scheme 1:
Grignard reaction of aldehyde 3 and oxidation of the resulting mixture of alcohols 4–7. Reagents an...