Rearrangement of 1-aryl-2,2-Dichloro-1-Alkanones and 1-Aryl-2,2-Dichloro-1-Alkanols with Methylmagnesium Iodide

Autor:	Roland Verhé, Niceas Schamp, Laurent De Buyck, Norbert De Kimpe
Rok vydání:	2010
Předmět:	chemistry.chemical_classification Pinacol Aryl Kornblum–DeLaMare rearrangement Iodide Ether General Chemistry Sigmatropic reaction Magnesium iodide Medicinal chemistry Carroll rearrangement chemistry.chemical_compound chemistry Organic chemistry
Zdroj:	Bulletin des Sociétés Chimiques Belges. 88:719-735
ISSN:	0037-9646
DOI:	10.1002/bscb.19790880910
Popis:	1-Aryl-2,2-dichloro-1-alkanones were shown to rearrange with methyl magnesium iodide in ether under reflux into highly sterically hindered alkohols. The mechanism proceeds by a pseudo pinacol type rearrangement of the initially formed carbonyl adduct. The mechanism of the rearrangement was proven by the synthesis of authentic reaction intermediates. The rearrangement was also extended to 1-aryl-2,2-dichloro-1-alkanols which behaved analogously towards methylmagnesium iodide.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::aaa42544e0823ec2935f3f256cc9dbbc https://doi.org/10.1002/bscb.19790880910 Zobrazit plný text záznamu