Stereochemistry of the Bucherer–Bergs and Strecker reactions of tropinone, cis-bicyclo[3.3.0]octan-3-one and cis-3,4-dimethylcyclopentanone

Autor:	Emilia Santos, Sin Cheong Wong, Carmen Avendaño, Gregorio G. Trigo, John T. Edward
Rok vydání:	1979
Předmět:	chemistry.chemical_compound chemistry Bicyclic molecule Stereochemistry Group (periodic table) Organic Chemistry Tropinone General Chemistry Carbon-13 NMR Catalysis
Zdroj:	Canadian Journal of Chemistry. 57:1456-1461
ISSN:	1480-3291 0008-4042
DOI:	10.1139/v79-238
Popis:	The tropane-3-spiro-5′-hydantoin (α isomer) obtained from tropinone by the Bucherer–Bergs reaction has been shown by 13C nmr and X-ray diffraction studies to have the 4′-carbonyl group in the equatorial position; the β isomer, obtained via the Strecker reaction, has this group axial. The results of these two reactions on cis-bicyclo[3.3.0]octan-3-one and on cis-3,4-dimethylcyclopentanone show, on the basis of the 1H nmr, 13C nmr, and X-ray diffraction studies of the products, a stereochemical course related to the preferred conformation of the cyclopentane rings.
Databáze:	OpenAIRE
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