Functionalization of saturated hydrocarbons : high temperature bromination

Günbaş, Duygu Deniz
Although saturated hydrocarbons are readily available and extremely cheap starting materials, they can not be used in synthetic chemistry without prior activation. Efficient functionalization of alkanes leading to the production of useful organic chemicals in an industrial scale is of considerable interest for the chemical and pharmaceutical industries and remains a long-term challenge for chemists. In this respect, halogenations of hydrocarbons which leads to a variety of useful synthetic intermediates is an open avenue which deserves special attention. It is also noteworthy to mention that efficient methods for selective functionalization of saturated bicyclic hydrocarbons still remains elusive, albeit a number of methods employing various reagents have been developed for the CH bond activation of open chain and monocyclic alkanes. Herein, we will investigate the high temperature bromination reactions as a method for functionalization of saturated bicyclic hydrocarbons such as octahydropentalene (1), octahydro-1H-indene (2) and 1a,2,7,7a-tetrahydro-1H-cyclopropa[b]naphthalene (3). The scope and the limitations of the reaction will reveal the regio-and stereoselectivity. Furthermore, formation mechanism of the products will be discussed and the chemistry of these compounds will be extended for further functionalization.


Functionalization of saturated bicyclic hydrocarbons: high temperature bromination
Özer, Melek Sermin; Balcı, Metin; Department of Chemistry (2011)
Although hydrocarbons are readily available and extremely cheap starting materials, they cannot be used in synthetic chemistry without prior activation. The selective functionalization of saturated hydrocarbons under mild conditions is of both biochemical and industrial importance. Initially, saturated hydrocarbons such as octahydro-1H-indene 80, octahydro-1H-4,7-methanoindene 81 and bicyclo[4.2.0]octan-7-one 82 were synthesized as starting materials. Then high temperature bromination reactions of these sat...
Oxidative ring opening reactions of a-hydroxy ketones
Aybey, Ayşe; Demir, Ayhan Sıtkı; Department of Chemistry (2008)
Chiral polyfunctionalized 1,5-dicarbonyl compounds are important synthetic intermediates and starting materials for many biologically active compounds so their synthesis has a great importance in the literature. In the first step, 1,3-cyclohexandione and other b-diketone derivatives are protected under acid catalyzation and their corresponding b-keto enol ether derivatives are obtained. These b-keto enol ethers are then converted to a-acetoxy enones in racemic form by Mn(OAc)3 mediated oxidation. Enzymatic ...
Oxidation of Primary Alcohols to Aldehydes with N-Halamine-Containing Polymers
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Polymeric N-halamines have been previously employed for organic reactions such as sulfide oxidation. In the present study, we employed polymeric N-halamines to oxidize primary alcohols selectively to the corresponding aldehydes in excellent yields. After reaction, the polymers can be recycled and then reused for the next reaction process.
Reactions of 2-substituted epichlorohydrins
Tanyeli, Cihangir; Akhmedov, IM; Ozgul, E; Kandemir, CG (Informa UK Limited, 1996-01-01)
2-Substituted epichlorohydrins have been synthesized by starting with 1,2-dichloro acetone and various alkyl and aryl halides via dichlorohydrins followed by cyclization. The reactive 2-substituted epichlorohydrins were subjected to nucleophilic attacking of azide and cyanide ions to afford corresponding beta-azido alcohols and alpha,beta-unsaturated nitriles.
Synthesis of various camphor-based chiral pyridine derivatives
Işık, Murat; Tanyeli, Cihangir; Department of Chemistry (2005)
Chiral aromatic nitrogen heterocycles are finding many applications in asymmetric organic synthesis, particularly as ligands in the preparation of chiral metal complexes. Since camphor-based chiral auxiliaries are known to be especially effective, a number of pyridines fused to the camphor skeleton have been reported. It is well known that nicotinic acid and its derivatives exhibiting qualitatively the biological activity of nicotinamide, which acts as an electron acceptor in many biological redox reactions...
Citation Formats
D. D. Günbaş, “ Functionalization of saturated hydrocarbons : high temperature bromination,” M.S. - Master of Science, Middle East Technical University, 2006.