The 2,4,6-Trimethoxyphenyl Unit as a Unique Protecting Group for Silicon in Synthesis and the Silylation Potential of (2,4,6-Trimethoxyphenyl)silanes

Autor:	Jennifer B. Nätscher, Friedrich Popp, Jürgen O. Daiss, Reinhold Tacke, and Christian Burschka
Rok vydání:	2007
Předmět:	Silanes Silylation Organic Chemistry Regioselectivity Silane Inorganic Chemistry chemistry.chemical_compound chemistry Nucleophile Reagent Organic chemistry Physical and Theoretical Chemistry Selectivity Protecting group
Zdroj:	Organometallics. 26:6014-6028
ISSN:	1520-6041 0276-7333
Popis:	A series of triorganyl(2,4,6-trimethoxyphenyl)silanes containing various combinations of acid-labile protecting groups for silicon, including allyl, 2,6-dimethoxyphenyl, mesityl, 4-methoxyphenyl, 1-naphthyl, and phenyl, were synthesized and characterized. These compounds served as reagents in a series of experiments to determine the selectivity of the cleavage of the 2,4,6-trimethoxyphenyl group in the presence of the aforementioned groups using an ethereal hydrogen chloride solution to obtain synthetically useful chlorosilanes. Additionally, the silylation potential of trimethyl-, methyldiphenyl-, and triethyl(2,4,6-trimethoxyphenyl)silane under mild (0−35 °C), acidic conditions with O-, N-, and S-nucleophiles was examined. These silylation reagents exhibit both chemo- and regioselectivity with respect to the tested nucleophiles, are neither moisture nor air sensitive and thus easy to handle, and produce a relatively inert byproduct, 1,3,5-trimethoxybenzene, which is recyclable.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::0a9dc4e2d1ca5cf85626cc6c79d051bd https://doi.org/10.1021/om700805p Zobrazit plný text záznamu