Criss-cross cycloadducts rearrangement induced by electrophiles

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Authors	ZACHOVÁ Hana MAN Stanislav TARABA Jan POTÁČEK Milan
Year of publication	2005
Type	Article in Proceedings
Conference	XLVIII Zjazd Polskiego towarzystwa chemicznego Poznaň 2005
MU Faculty or unit	Faculty of Science
Citation
Field	Organic chemistry
Keywords	rearrangement; criss-cross cycloaddition; homoallenylazines
Description	Intramolecular criss-cross cycloaddition reaction of symmetrical homoallenylazines is a specific type of successive 1,3-dipolar cycloaddition reactions. New fused tetracyclic compounds are formed in high yields by this reaction. In acidic conditions the criss-cross cycloadduct rearranges to completely new structure of heterocyclic compound with two six-membered and two five-membered rings. This new rearrangement was firstly monitored in the presence of reducing agent (NaBH3CN). A similar reaction is observed when an electrophile reagent instead of acid is used. When reducing agent is not used the stable quartery iminium salt is isolated.
Related projects:	Structure and character of bonding, properties and analysis of synthetic and natural molecular ensembles