Intramolecular ring closure via ether bond in reaction of α,α′-halogeno bicyclo[3.3.1]nonanediones under basic conditions

Autor:	Albinas Žilinskas, Eugenius Butkus, Sigitas Stončius, Rytis Kubilius
Rok vydání:	1999
Předmět:	chemistry.chemical_compound chemistry Bicyclic molecule Stereochemistry Intramolecular force Halogenation Ether Favorskii reaction Stereoselectivity Ring (chemistry) Medicinal chemistry Sodium methoxide
Zdroj:	Journal of the Chemical Society, Perkin Transactions 1. :1431-1436
ISSN:	1364-5463 0300-922X
Popis:	The stereoselectivity of halogenation of bicyclo[3.3.1]nonan-2-one 1 and bicyclo[3.3.1]nonane-2,6-dione 2 with molecular bromine and chlorine was studied. The transformation of α-bromo- and chloro-bicyclo[3.3.1]nonanones 3–5 under Favorskii reaction conditions was studied. The reaction of α,α′-dihalogeno diones in the presence of sodium methoxide, ethoxide, propoxide and potassium cyanide led to the intramolecular ring closure via C–O bond formation giving the highly functionalized chiral 2-oxatricyclo[4.3.1.03,8]decane (2-oxaprotoadamantane) structure. Enantiomers of this cage structure were resolved by chiral GLC. The intramolecular ring closure pathway involving the intermediate alkoxybicyclo[3.3.1]nonanolate structure was proposed.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::a645a08540fb6f95ab66996a6099c59d https://doi.org/10.1039/a901620a Zobrazit plný text záznamu