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Dihaloimidazolidinediones as Versatile Halodehydrating Agents
Author(s) -
Moerdyk Jonathan P.,
Bielawski Christopher W.
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201403407
Subject(s) - geminal , halide , halogen , alkyl , chemistry , substitution (logic) , nucleus , carbon fibers , combinatorial chemistry , functional group , medicinal chemistry , organic chemistry , computer science , psychology , algorithm , neuroscience , composite number , programming language , polymer
Dihaloimidazolidinediones containing geminal dibromides, dichlorides, or diiodides were synthesized and used to transform various alcohols to their corresponding alkyl halides in high yields and under mild conditions. High functional group tolerance and, in many cases, high selectivities were observed. Efforts toward elucidating the mechanism revealed that significant charge build‐up may occur at the eventual halogen containing carbon nucleus prior to substitution.