ISSN:
0894-3230
Keywords:
Organic Chemistry
;
Physical Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
,
Physics
Notes:
An MNDO study was made of the gas-phase thermal isomerization of isoxazole to explore theoretically the proposed reaction mechanism. The results showed that isoxazole isomerizes through an azirine, as an intermediate, to oxazole via a nitrile ylide or to ketenimine, with similar activation energies, and that the first step is rate limiting, in agreement with the experimental results. These results also show that isomerization to a nitrile is possible, but in this case the energy barrier is grater than the corresponding isomerization to oxazole. The MNDO study also supports a concerted process for the rate-limiting step, as reported earlier on the basis of experimental studies.
Additional Material:
8 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/poc.610030910
