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Volumn 6, Issue 11, 2000, Pages 2063-2068

8-Phenyl-10,10a-dihydropyrido[1,2-a]azepines by 1,7-electrocyclization of conjugated pyridinium ylides - rationalization of the periselectivity

Author keywords

Azepines; Cyclizations; Heterocycles; Pericyclic reactions; Periselectivity

Indexed keywords

AZEPINE DERIVATIVE; PYRIDINIUM DERIVATIVE;

EID: 0034595709     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (19)

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