Rani, Rajan; Dr.Radhakrishnan, K V(Cochin University Of Science And Technology, April , 2013)
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Abstract:
The reactions involving fulvenes and its derivatives have received a great
deal of attention over the years in synthetic organic chemistry. Functionalizations
of fulvenes provide versatile and powerful approaches to various polycyclic
systems and natural products. They serve as versatile intermediates in the
construction of various ring systems through inter- as well as intramolecular
cycloadditions. Compared to the rich literature on the cycloaddition reactions of
pentafulvenes, much less attention has been paid to the synthetic utilization of
their cycloadducts. Tactical manipulations on the chosen adduct offer the
prospects for designing a variety of useful molecular skeletons.
Addition of heterodienophiles to fulvenes offers an efficient strategy towards
the synthesis of azabicyclic olefins. However, there have been no serious attempts
to study the synthetic utility of these substrates. In this context and with the
intention of utilizing pentafulvenes towards synthetically important molecules, author
decided to explore the reactivity of pentafulvene derived azabicyclic olefins. Our
attention was focused on the synthetic potential associated with the ring opening
of fulvene derived bicyclic hydrazines under palladium catalysis. It was envisioned
that the desymmetrization of these adducts using various soft nucleophiles will
provide a novel access to synthetically and biologically important alkylidene
cyclopentenes. The investigations along this line form the focal theme of this
thesis entitled “PALLADIUM CATALYZED CARBONCARBON/
CARBON-HETEROATOM BOND FORMATION REACTIONS
UTILIZING PENTAFULVENE DERIVED BICYCLIC HYDRAZINES
Description:
Organic
Chemistry Section, National Institute for Interdisciplinary Science and Technology