Intramolecular 1,2-Aroyl Migration in Spiro Donor–Acceptor Cyclopropanes: Formation of 1,4-Naphthoquinones and 1-Naphthols as Ring-Expansion Products
Franklin Leslin Daniel,
Kannupal Srinivasan
Abstract:Most of the known rearrangement reactions of donor−acceptor cyclopropanes (DACs) involve the migration of cationic carbon atom to anionic carbon or heteroatoms in 1,3-or 1,4-positions. In the present work, we observed that spiro DACs based on 1,3-indanedione or 1-indanone moiety undergo intramolecular 1,2-aroyl migration when treated with titanium(IV) chloride to afford 1,4-naphthoquinones and α-naphthols readily. The reactions take place through the formation of putative 1,3-dipolar intermediates, followed by… Show more
A caesium carbonate-promoted reaction of nitro-substituted donor–acceptor cyclopropanes (DACs) with primary aromatic amines in water provides convenient access to β-enamino malonates under mild reaction conditions.
A caesium carbonate-promoted reaction of nitro-substituted donor–acceptor cyclopropanes (DACs) with primary aromatic amines in water provides convenient access to β-enamino malonates under mild reaction conditions.
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