Beilstein J. Org. Chem.2016,12, 2189–2196, doi:10.3762/bjoc.12.209
variety of substituents on cyclopropanatedoxabenzonorbornadiene. With unsymmetrical C1-substituted cyclopropanated 7-oxabenzonorbornadienes, the regioselectivity of the reaction was excellent, forming only one regioisomer in all cases.
Keywords: alcohol nucleophiles; C1 substitution; cyclopropanated
nucleophile at the internal cyclopropane carbon C, which could induce ring expansion to form seven-membered ring 12 .
In this paper, we aim to explore the use of a palladium catalyst with an alcohol nucleophile on the ring opening of cyclopropanatedoxabenzonorbornadiene with the goal of determining which
type of ring-opening pathway it follows. This complements previous studies by our group involving the ring opening of cyclopropanatedoxabenzonorbornadiene through the novel use of a transition metal catalyst. Using a transition metal catalyst could reveal new ring-opening pathways and provide further
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Graphical Abstract
Scheme 1:
Various chemical transformations of 7-oxabenzonorbornadiene 1.