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1,3-Dipolar Cycloadditions, 99. Nitrones and Thiones: Cycloadditions and Surprising Metathesis Reactions

✍ Scribed by Giera, Henry ;Huisgen, Rolf

Publisher
John Wiley and Sons
Year
1997
Tongue
English
Weight
568 KB
Volume
1997
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

Nitrone 4 combines with alicyclic thioketones at room temp. affording 1,4,2‐oxathiazolidines. Steric hindrance in both reactants affects the cycloaddition/cycloreversion equilibria, but the mobility is still high; the low π‐LUMO energies of CS are responsible for the superdipolarophilic character. Nitrone 4 and thiobenzophenone enter into a metathesis reaction which was traced back to a sulfhydrogenolysis pathway; H~2~S acts as a catalyst. An analogous metathesis between nitrone 4 and benzaldehyde involves a hydrolysis.

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## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v