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Current Organic Chemistry


ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

Allenes as Dipolarophiles and 1,3-Dipole Precursors: Synthesis of Carbocyclic and Heterocyclic Compounds

Author(s): Teresa M. V. D. Pinho e Melo

Volume 13, Issue 14, 2009

Page: [1406 - 1431] Pages: 26

DOI: 10.2174/138527209789055090

Price: $65


The use of allene derivatives in the 1,3-dipolar cycloaddition either as dipolarophiles or 1,3-dipole precursors is discussed. Allenes participate in cycloadditions with a variety of 1,3-dipoles namely nitrile oxides, nitrones, carbonyl ylides, nitrile imines, azides and diazocompounds. They also react as the 2??-component in other annulation reactions such as the cycloaddition of ambident 1,3-dipolar species generated from benzimidazole carbenes and isothiocyanates, palladium- catalyzed overall intramolecular [3+2] cycloaddition with alkylidenecyclopropanes and rhodium(I)-catalyzed formal [3+2] annulation reaction of chromium alkenyl(methoxy)carbene complexes. The reactivity of allenes as 1,3-dipole precursors and the subsequent annulation reactions are also covered. Allenes can be used to generate nitrones and other dipolar species can be obtained from allenylazines, via π-allylPd intermediates generated from allenes and from the reaction of allenes with phosphines.

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