Beilstein J. Org. Chem.2014,10, 307–315, doi:10.3762/bjoc.10.28
afforded 1,1,3,3-tetramethylindan-2,2-dicarboxylic acid. Brominativedeoxygenation of the ketones furnished two one-sidedly overcrowded bromoalkenes. Some presently relevant properties of the above Cl,K-carbenoid are provided in Supporting Information File 1.
Keywords: brominativedeoxygenation; carbenoid
NMR signals). The constitution of 40 followed from its ready decarboxylation in CDCl3 solution at rt to regenerate acid 10 within four days.
Conversion of the ketone 38a into bromoalkene 42a through brominativedeoxygenation [42][43] with tribromide 41 was slow in hot chloroform but almost complete
generation of dianion 37 of acid 10 (Scheme 6). Nevertheless, such one-sided shielding in the product ketone does not prevent the incorporation of a second nucleophile, affording a tertiary alcohol with a substantially impeded internal mobility. Final brominativedeoxygenation of the ketones can yield
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Graphical Abstract
Scheme 1:
1,1,3,3-Tetramethylindane derivatives are preferable.