ChemInform Abstract: Strained Rings to Assess the 'endo Preference' of 2-Alkyl Branched 2-Alkenylpotassium Species

Autor:	Martina Kotthaus, Manfred Schlosser
Rok vydání:	2010
Předmět:	chemistry.chemical_classification Allylic rearrangement Chemistry Potassium Caryophyllene chemistry.chemical_element General Medicine Medicinal chemistry Terpene Hexane chemistry.chemical_compound Deprotonation Butyllithium Alkyl
Zdroj:	ChemInform. 29
ISSN:	1522-2667 0931-7597
DOI:	10.1002/chin.199834106
Popis:	Upon deprotonation using trimethylsilylmethylpotassium or butyllithium in the presence of potassium tert-butoxide, two allylic organopotassium species are generated from the (E)-isomeric caryophyllene and the (Z)-isomeric isocaryophyllene. Torsional equilibration occurs slowly at -50 DegC (in THF) and rapidly at 0 DegC (in hexane) to afford endo/exo-mixts. of about 95:5 (as evidenced by the isomeric compn. of the trapping products). The relative thermodn. stabilities of the two stereoisomeric organometallic intermediates can be derived by mere superposition of ring-strain differences and the qendo preferenceq of open-chain (alkylalkenyl)potassium compds. [on SciFinder (R)]
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::3eef82fce859e03043e46d44d8cef6d0 https://doi.org/10.1002/chin.199834106 Zobrazit plný text záznamu Plný text