614-43-7Relevant articles and documents
1,3-Dibromo-5,5-dimethylhydantoin as a Precatalyst for Activation of Carbonyl Functionality
?ebular, Klara,Bo?i?, Bojan ?.,Stavber, Stojan
supporting information, (2019/08/01)
Activation of carbonyl moiety is one of the most rudimentary approaches in organic synthesis and is crucial for a plethora of industrial-scale condensation reactions. In esterification and aldol condensation, which represent two of the most important reactions, the susceptibility of the carbonyl group to nucleophile attack allows the construction of a variety of useful organic compounds. In this context, there is a constant need for development of and improvement in the methods for addition-elimination reactions via activation of carbonyl functionality. In this paper, an advanced methodology for the direct esterification of carboxylic acids and alcohols, and for aldol condensation of aldehydes using widely available, inexpensive, and metal-free 1,3-dibromo-5,5-dimethylhydantoin under neat reaction conditions is reported. The method is air- and moisture-tolerant, allowing simple synthetic and isolation procedures for both reactions presented in this paper. The reaction pathway for esterification is proposed and a scale-up of certain industrially important derivatives is performed.
Selective mono-fluorination of diols via a cyclic acetal of N,N-diethyl-4-methoxybenzamide
Suwada, Mitsuhiro,Fukuhara, Tsuyoshi,Hara, Shoji
, p. 1121 - 1125 (2008/02/10)
Selective mono-fluorination of 1,2- and 1,3-diols was achieved using N,N-diethyl-4-methoxybenzamide diethyl acetal and Et3N-3HF. The reaction proceeds through a cyclic acetal of the benzamide, and only one hydroxy group was fluorinated and anot
CHEMOSELECTIVE FLUORINATION FOR PRIMARY ALCOHOLS
Shimizu, Makoto,Nakahara, Yuko,Yoshioka, Hirosuke
, p. 4207 - 4210 (2007/10/02)
Primary alcohols and their silylated derivatives are selectively fluorinated by tetraalkylammonium fluoride and aryl (or alkyl) sulfonyl fluoride.