126865-07-4Relevant academic research and scientific papers
Copper-Catalyzed Multicomponent Reaction of DABCO·(SO2)2, Alcohols, and Aryl Diazoniums for the Synthesis of Sulfonic Esters
Wang, Yang,Deng, Lingling,Deng, Yu,Han, Jianlin
, p. 4674 - 4680 (2018/04/26)
A Cu-catalyzed multicomponent cascade reaction of DABCO·(SO2)2 (DABSO), alcohol, and aryl diazonium tetrafluoroborate was developed which afforded sulfonic esters in moderate to good chemical yields. In this reaction, the SO2 surrogate DABSO was used for the first time in the synthesis of sulfonic aliphatic esters. This multicomponent reaction was carried out under mild conditions and tolerated a wide range of substrates, which provides a new and efficient strategy for the synthesis of sulfonic esters.
Intramolecular Reactions. Part 12. Ring Size and Leaving Group Effects on Inter- and Intra-molecular Nucleophilic Substitution by Carbanions
Bird, Roger,Griffiths, Gwerydd,Griffiths, Gwynfor F.,Stirling, Charles J. M.
, p. 579 - 584 (2007/10/02)
In cyclisations of aryl ο-halogenoalkyl ketones to aryl cycloalkyl ketones with base, cyclopropanes are formed up to 23000 times faster than cyclopentanes.Hydrogen-deuterium exchange experiments and very low bromide-chloride ratios (1.9) for three-membered ring formation are consistent with rate-determining deprotonation of the ketone.By contrast, in five-membered ring formation, hydrogen-deuterium exchange adjacent to the carbonyl group occurs much faster than cyclisation and the chloride-bromide ratio is 'normal' at 99.In formation of arylsulphonylcyclopropanes from arylsulphonylpropyl arenesulphonates, the Hammett ρ value for the leaving group is +1.7, and for intermolecular substitution by bis-sulphonyl stabilised carbanions, +1.2.Attempts to obtain ρLG values for five-membered ring formation were frustrated by competing intermolecular reactions.The results are discussed against the background of previous work on ring formation by intramolecular nucleophilic substitution.
