ISSN:
1434-4475
Keywords:
α-Carbonyl-spiro-oxiranes
;
Enolbetaines
;
Nucleophilic Substitution
;
Spiro-dioxoles
;
Spiro-oxazoles
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Abstract Nucleophilic substitution at the spiro carbon atom as well as the CH2-group takes place with spiro-oxiranes1,6 and7, whose spiro carbon atom bear electron withdrawing substituents. In some cases by elimination of formaldehyde a transformation to the corresponding reductone systeme (5,11,16) is observed. In other cases, e.g. with tertiary amines, betaines (2,9,12) are formed, which by elimination of the base rearrange to dioxolenes (3,10). Addition of polar reagents like aryl isocyanate or chloral leads to ring expansion of the threemembered ring to form the five ring systems17,18,20,22 or24.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00799242
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