Generation and Characterization of Alkyl-Substituted m-Xylylenes in Fluid Solution at Room Temperature

Autor:	Joseph J. Gajewski, Gitendra C. Paul, Andrea M. Gortva, Ming Jing Chang
Rok vydání:	1994
Předmět:	Trimethylsilyl Dimer General Chemistry Methylenecyclopropane Biochemistry Medicinal chemistry Enol Catalysis Cyclopropane chemistry.chemical_compound Colloid and Surface Chemistry chemistry Trifluoromethanesulfonate Isopropyl Fulvene
Zdroj:	Journal of the American Chemical Society. 116:5150-5154
ISSN:	1520-5126 0002-7863
DOI:	10.1021/ja00091a018
Popis:	Fluoride ion induced generation of isobutylidene from isopropyl trimethylsilyl ketone enol triflate in the presence of 6,6-dimethylfulvene gives the [2.2]-m-cyclophane dimer of [alpha],[alpha],[alpha][prime],[alpha][prime]-tetramethyl-m-xylylene. When isobutylidene is added to 6,6-bis(trideuteriomethyl)fulvene, the [sup 13]C NMR spectrum of the dimer reveals three quaternary carbons in a 1:1:1 ratio, progressively shifted upfield to suggest that two dimers are formed. Saturation of the reactant solutions with dioxygen resulted in no dimer formation despite undimished loss of reactants. A control experiment indicated that dioxygen does not affect the formation of the methylenecyclopropane from cyclohexene and isobutylidene. Reaction of 6-cyclopropyl-6-methylfulvene with isobutylidene gave dimers with intact cyclopropane rings. Addition of isbutylidene 6-tert-butyl-6-methylfulvene resulted in a non-cyclophane dimer. 26 refs.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::213960c7b90ffa2ae5d8e5df55aba005 https://doi.org/10.1021/ja00091a018 Zobrazit plný text záznamu