Ionic hydrogenations using boron trifluoride hydrate. Reductions of polycyclic aromatics

Autor:	John W. Larsen, Laurence W. Chang
Rok vydání:	1979
Předmět:	Anthracene chemistry.chemical_compound chemistry Hydride Organic Chemistry Triethylsilane Phenanthrene Benzene Anisole Medicinal chemistry Boron trifluoride Naphthalene
Zdroj:	The Journal of Organic Chemistry. 44:1168-1170
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo01321a033
Popis:	Results obtained using the boron trifluoride monohydrate and triethylsilane pair are reported. The following compounds did not undergo hydrogenation: naphthalene, phenanthrene, 1-methylnaphthalene, ..beta..-naphthalenethiol, phenol, anisole, toluene, and benzene. These compounds were reduced and their reaction products were tabulated: anthracene, naphthacene, 1-hydroxynaphthalene, 2-hydroxynaphthalene, 1-methoxynaphthalene, 2-metholxynaphthalene, 1-naphthalenethiol, ..cap alpha..-tetralone, 2-acetonaphthalene, and adamantanone. Measurements were made using gas chromatography, mass spectra, and NMR. The mechanism of this kind of reaction appears to be protonation followed by hydride abstraction which is rate determining.
Databáze:	OpenAIRE
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