Carbon-containing nucleophiles opening with

Epoxide opening with nucleophiles occurs at the less substituted carbon atom of the oxlrane ting. Cataiytic hydrogenolysis yields the more substituted alcohol. The scheme below contains also an example for trons-dibromination of a C—C double bond followed by dehy-drobromination with strong base for overall conversion into a conjugated diene. The bicycKc tetraene then isomerizes spontaneously to the aromatic l,6-oxido[l0]annulene (E. Vogel, 1964). 

A review of the metal-catalysed ring opening of achiral epoxides by achiral carbon-, sulfur-, nitrogen- and halogen-containing nucleophiles and kinetic resolution of racemic epoxides has been published.24 The review also discusses the reactions of chiral bases with epoxides that give allylic alcohols. 

The diol-epoxide contains a reactive carbon center, namely the C-10 position, which can open to form a carbonium ion that is susceptible to nucleophilic attack (Scheme 3.4). The predominant nucleophile among DNA bases is guanine, which preferentially interacts with the carbonium ion at the N2-amine position of guanine to form the BaP-N 2-guanine adduct. The epoxide bond of the diol-epoxide metabolite is particularly resistant to hydrolysis because it is located in the Bay region of the BaP molecule, where steric hindrance prevents the attack of hydrolytic enzymes, such as epoxide hydrolase. 

Arylene ether/imide copolymers were prepared by the reaction of various amounts 4,4 -carbonylbis[Ar-(4 -hydroxyphenyl)phthalimide] and 4,4 -biphenoi with a stoichiometric portion of 4,4 -dichlorodiphenyl sulfone in the presence of potassium carbonate in NMP/CHP [55]. To obtain high molecular weight polymer, the temperature of the reaction was kept below 155 °C for several hours before heating to >155°C in an attempt to avoid undesirable side reactions such as opening of the imide ring. The imide ring is not stable to conditions of normal aromatic nucleophilic polymerizations unless extreme care is exercised to remove water. Special conditions must be used to avoid hydrolysis of the imide as previously mentioned in the section on Other PAE Containing Heterocyclic Units and as practiced in the synthesis of Ultem mentioned in the Historical Perspective section. 

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