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Norbornadiene as a Universal Substrate for Organic and Petrochemical Synthesis

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A wide range of rare polycyclic hydrocarbons can be obtained through catalytic processes involving norbornadiene (NBD). The problem of selectivity is crucial for such reactions. The feasibility of controlling selectivity… Click to show full abstract

A wide range of rare polycyclic hydrocarbons can be obtained through catalytic processes involving norbornadiene (NBD). The problem of selectivity is crucial for such reactions. The feasibility of controlling selectivity and reaction rate has been shown for cyclic dimerization, co-dimerization, isomerization and allylation of NBD. Kinetic rules have been scrutinized. Consistent mechanisms have been proposed. Factors affecting directions of the reactions and allowing us to obtain individual stereoisomers quantitatively, have been established. A series of novel unsaturated compounds has been synthesized; they incorporate a set of double bonds with different reactivity and can find an extremely wide range of applications. Eurasian ChemTech Journal 3 (2001) 73-90  2001 al-Farabi Kazakh St.Nat. University Introduction The importance of NBD and its derivatives in various fields of human activity is growing. More and more new applications are being discovered for these compounds. Since they were first obtained less than 50 years ago, these substances have been successfully utilized in medicine, agriculture, rocketry, syntheses of polymers with unique properties, microelectronics, and as solar energy converters. The number of patents concerned with synthesis and application of NBD derivatives and norbornene-2 (NBN) had exceeded 100 hundreds by the year 2000. Due to their unique structure, compounds with NBD and NBNmoieties are achieving the leading positions in contemporary chemistry and chemical technology [1-3]. It should be strongly emphasized that NBD itself and some of its simplest derivatives are obtained from chemicals, produced on a large scale during oil processing [4]. They are cyclopenta-1,3-diene (CPD), acetylene, alkenes, and alkadienes with various structures. Production of CPD can easily be combined with synthesis of other petrochemical products, for example ethylene. Today, a large proportion of CPD cannot be duly utilized, so it is very important to search for new ways of its utilization. Even though NBD has extremely rich synthetic possibilities, its utilization as a universal substrate is rather limited, since NBD-derivatives can form all kinds of isomers: skeleton, regio, stereo, enantio ones. A resultant mixture of isomeric products is often difficult to separate and analyze, and the consumption of reagents may become excessive. All this restricts widespread use of NBD. Metal-complex catalysis is very interesting and attractive for solving various problems connected with selectivity [5]. By applying its tenets and methods to reactions involving NBD and its derivatives, by scrutinizing mechanisms of reactions, we can control structure and range of regioand stereo isomers, synthesize new compounds of this type, and can make their production sensible from technological and economical points of view. The present article bases on several research directions concerned with application of the above-mentioned methods in some of the most promising processes involving NBD.

Keywords: universal substrate; nbd derivatives; norbornadiene universal; petrochemical; synthesis

Journal Title: Eurasian Chemico-Technological Journal
Year Published: 2017

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