ISSN:
0947-3440
Keywords:
Nitrones
;
Electrophilic acetylenes
;
2,3-Dihydroisoxazoles
;
Cycloadditions
;
Rearrangements
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The readiness of 4-isoxazolines, the 1,3-cycloadducts of nitrones to acetylenic compounds, to undergo rearrangement is notorious. The cycloadducts of the ketonitrones 5 and 6 to dimethyl acetylenedicarboxylate, dicyanoacetylene, and methyl propiolate were isolated and characterized. The 4-isoxazolines 7 and 8 harbor the tetramethylcyclobutanone ring; they isomerize (7 at 45°C, 8 at -10°C) to enamine β-carbonyl compounds 16 and 17 which are derived from the ring-enlarged tetramethylpyrrolidin-3-one. The structure of 16 was elucidated by X-ray analysis.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199719970810
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