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Synlett 1998; 1998(9): 950-957
DOI: 10.1055/s-1998-1826
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Cycloaddition Reactions of Heptafulvenes: An Overview

Vijay Nair* , G. Anilkumar
  • *Organic Chemistry Division, Regional Research Laboratory (CSIR), Trivandrum- 695 019, India; Fax 91-4 71-49 17 12; E-mail: gvn@csrrltrd.ren.nic.in
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Publication History

Publication Date:
31 December 2000 (online)

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Heptafulvenes exhibit multiple reaction profiles in cycloaddition reactions. 8-Alkyl and 8-alkoxy heptafulvenes are shown to be excellent 8π partners with electron deficient dienophiles. Heptafulvene chromium carbonyl complex undergoes [6 + 4] addition with butadiene. The [4 + 2] cycloaddition reactions of heptafulvenes yield complex bicyclo systems. Isolated examples of heptafulvene participating as a 2π addend are also reported. Cyclohepta[b]furan-2-one, a tethered heptafulvene derived from tropolone, undergoes both [8 + 2] and [4 + 2] additions.

heptafulvenes - 2H-cyclohepta[b]furan-2-ones - cycloaddition profiles