Formation of reactive o-quinone methides from the reaction of trimethylsilyl(methyl)-substituted 1,4-benzoquinones with nucleophiles

Autor:	Harold W. Moore, John E. Ezcurra, Kostas Karabelas
Rok vydání:	2005
Předmět:	Silylation Trimethylsilyl Dimer Organic Chemistry Reactive intermediate General Medicine Ring (chemistry) Biochemistry Medicinal chemistry Reaction rate chemistry.chemical_compound chemistry Nucleophile Drug Discovery Michael reaction Organic chemistry Derivative (chemistry)
Zdroj:	Tetrahedron. 61:275-286
ISSN:	0040-4020
Popis:	o-Quinone methides are formed from the reaction of nucleophiles with trimethylsilyl(methyl)-1,4-benzoquinones. These reactive intermediates are trapped by excess nucleophile to form substituted quinones following oxidation. In addition, varying amounts of a symmetrical dimer and a xanthen derivative were observed. The influence of different nucleophiles and ring substituents on the rate of reaction have been studied, and are consistent with rate-limiting formation of a vinylogous enolate initiated by attack of the nucleophile on the silyl group.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::6e6aedc02f4596c7f3130a14532263f3 https://doi.org/10.1016/j.tet.2004.09.052 Zobrazit plný text záznamu Full Text from ScienceDirect