2876-63-3Relevant articles and documents
Stereoselective Ketone Rearrangements with Hypervalent Iodine Reagents
Malmedy, Florence,Wirth, Thomas
supporting information, p. 16072 - 16077 (2016/10/30)
The first stereoselective version of an iodine(III)-mediated rearrangement of arylketones in the presence of orthoesters is described. The reaction products, α-arylated esters, are very useful intermediates in the synthesis of bioactive compounds such as ibuprofen. With chiral lactic acid-based iodine(III) reagents product selectivities of up to 73 % ee have been achieved.
Synthesis of β-hydroxy and β-amino ketones from allylic alcohols catalyzed by ru(η5-C5Ph5)(CO)2Cl
Bartoszewicz, Agnieszka,Jezowska, Martina M.,Laymand, Kevin,Moebus, Juri,Martin-Matute, Belen
experimental part, p. 1517 - 1530 (2012/06/15)
An efficient method for the synthesis of β-hydroxy and β-amino ketones from allylic alcohols catalyzed by Ru(η5-C 5Ph5)(CO)2Cl is described. The influence of the stereoelectronic properties of the catalyst on the reaction outcome has been studied. Optimization of the reaction conditions supressed the formation of undesired side products such as saturated ketones, benzyl alcohols, and α,β-unsaturated ketones. Several aromatic and aliphatic allylic alcohols have been reacted with a large variety of aldehydes or imines to produce β-hydroxy ketones or β-amino ketones, respectively, in yields up to 99a%. Based on experimental data, a mechanism via ruthenium alkoxides and ruthenium aldoxides is proposed. In addition, a C-bound ruthenium enolate has been characterized. β-Hydroxy and β-amino ketones are synthesized from allylic alcohols and aldehydes or imines, respectively. The coupling reaction is catalyzed by Ru(η5-C5Ph5)(CO) 2Cl. Mechanistic investigations support a mechanism via ruthenium alkoxide intermediates.
DIRECTION OF ACYLATION OF NAPHTHALENE BY THE FRIEDEL-CRAFTS METHOD
Dumpis, M. A.,Kudryashova, N. I.,Khromov-Borisov, N. V.
, p. 1799 - 1803 (2007/10/02)
The Friedel-Crafts acylation of naphthalene by the halides of substituted and unsubstituted aliphatic carboxylic acids with various chain lengths (C2-C6) and various degrees of branching in the hydrocarbon chain was investigated.The effect of the solvent on the direction of acylation shows up during acylation by the least hindered acylating agents (acetyl chloride, acetyl bromide, chloroacetyl chloride, and bromoacetyl bromide).The α isomer is obtained preferentially in chloroform and the β isomer in nitrobenzene.With increase in the length and degree of branching of the hydrocarbon chain the β position of the naphthalene ring becomes the preferred direction of acylation.The main factor which determines the direction of Friedel-Crafts acylation in naphthalene is the steric factor.