Conrotatory Ring-Opening Reactions of Cyclopropyl Anions in Monocyclic and Tricyclic Systems

Autor:	Rosana Alvarez, Olalla Nieto Faza, de Lera Ar, Carlos Silva López
Rok vydání:	2004
Předmět:	chemistry.chemical_classification Bicyclic molecule Chemistry Stereochemistry Organic Chemistry Reaction path Physical and Theoretical Chemistry Conrotatory and disrotatory Ring (chemistry) Biochemistry Tricyclic
Zdroj:	Organic Letters. 6:901-904
ISSN:	1523-7052 1523-7060
DOI:	10.1021/ol036448x
Popis:	[reaction: see text] Only conrotatory transition structures were located by B3LYP6-311++G(3df, 2p) computations for the electrocyclic ring opening of cyclopropyl anions having different substituents (H, Me, CN). The transition structure for the similarly substituted cyclopropyl anion fused to a bicyclic system exhibits the same features, in apparent contradiction with the observed product. A reaction path where the direction of twist changes after the transition state provides an explanation alternative to those proposed in recent reports.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::dbdbf99d8d6231e0ea96b8ca0061c82c https://doi.org/10.1021/ol036448x Zobrazit plný text záznamu