The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 2-Chloropyridine 1-oxide( cas:2402-95-1 ) is researched.Recommanded Product: 2402-95-1.Wolfe, Saul; Yang, Kiyull; Weinberg, Noham; Shi, Zheng; Hsieh, Yih-Huang; Sharma, Rajendra Dev; Ro, Stephen; Kim, Chan-Kyung published the article 《Alkyl transfer with retention and inversion of configuration: reexamination of a putative [1s,4s] sigmatropic rearrangement》 about this compound( cas:2402-95-1 ) in Chemistry – A European Journal. Keywords: Tieckelmann rearrangement sigmatropic alkoxypyridineoxide ab initio; kinetics sigmatropic rearrangement alkoxypyridineoxide configuration retention. Let’s learn more about this compound (cas:2402-95-1).
The thermal rearrangement of 2-alkoxypyridine-1-oxides to 1-alkoxy-2-pyridones, which has been reported to proceed by an intramol. [1s,4s] sigmatropic migration of the alkyl group with retention of configuration and first-order kinetics, has been reexamined The intramol. barriers have been computed to be at least 20 kcal mol-1 higher than the reported exptl. barriers. An alternative bimol. mechanism, discovered computationally, has been confirmed by a variety of experiments including crossover studies, determination of solvent effects and secondary H/D isotope effects, and new kinetic and stereochem. studies. In the new mechanism there is an initial intermol. transfer of the alkyl group, with inversion of configuration, to the N-oxide. Depending on the nature of the alkyl group and the solvent, this is followed by a second transfer, also with inversion of configuration, of one of the alkyl groups of the cationic intermediate to one of the oxygens of the anionic intermediate. The product is then formed either without crossover, by a double inversion of one alkyl group, or with crossover by two single inversions of different alkyl groups. The proposed intermediates of this mechanism can be synthesized; they react to form a 1-alkoxy-2-pyridone at room temperature
In some applications, this compound(2402-95-1)Recommanded Product: 2402-95-1 is unique.If you want to know more details about this compound, you can contact with the author or consult more relevant literature.
Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem